MORPHOLINE-4-SULFONYL CHLORIDE

MORPHOLINE-4-SULFONYL CHLORIDE Property

Melting point:

72.36° C (Predicted)

Boiling point:

300℃

Density 

1.53

Flash point:

135℃

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

-10.95±0.20(Predicted)

form 

Solid or Liquid

color 

Colorless or White to Yellow

InChI

InChI=1S/C4H8ClNO3S/c5-10(7,8)6-1-3-9-4-2-6/h1-4H2

InChIKey

KXIBCCFSAMRWIC-UHFFFAOYSA-N

SMILES

N1(S(Cl)(=O)=O)CCOCC1

Safety

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN3265

HazardClass 

IRRITANT

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P321Specific treatment (see … on this label).

P332+P313IF SKIN irritation occurs: Get medical advice/attention.

P362Take off contaminated clothing and wash before reuse.

MORPHOLINE-4-SULFONYL CHLORIDE Chemical Properties,Usage,Production

Uses

Morpholine-4-sulfonyl chloride is used as an intermediate in organic synthesis for the preparation of benzothiazole compounds or thiazolecarboxamide derivatives and other organic heterocyclic compounds.

Synthesis

1. 10.0 mL of dichloromethane (CH2Cl2) was added to a 50 mL round bottom flask and cooled in an ice bath. 2. 0.300 mL of sulfuryl chloride (SO2Cl2) was slowly added to the cooled dichloromethane. 3. 213 mg of morpholine was dissolved in 3.0 mL of dichloromethane and slowly added to the above reaction mixture, kept cool in an ice bath. 4. 520 mg of trimethylamine was added and the reaction mixture was stirred at room temperature for about 2 hours. 5. Upon completion of the reaction, the product was dissolved with 20.0 mL of chloroform and subsequently washed with 20.0 mL of ice water. 6. The chloroform phase was separated, dried over magnesium sulfate (MgSO4) and filtered. 7. The filtrate was distilled under pressure to give 160 mg of morpholine-4-sulfonyl chloride in about 23.3% yield. 8. 70.0 mg of (R)-N-methyl-N-(pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine was added to a 5 mL round-bottomed flask and dissolved in 1.00 mL of dichloromethane. 9. 0.0390 mL morpholine-4-sulfonyl chloride was added, followed by 0.0590 mL N,N-diisopropylethylamine and stirred overnight at room temperature. 10. The reaction mixture was concentrated under pressure and the residue was purified by fast column chromatography (MeOH:CH2Cl2 = 2:98). 11. The purified grades were collected, concentrated under reduced pressure and further dried under vacuum to give 47.0 mg (R)-N-methyl-N-(1-(morpholinosulfonyl)pyrrolidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine in about 40.2% yield. 12. The product was analyzed by 1H NMR. 12. The product was structurally confirmed by 1H NMR and LRMS (ESI).

References

[1] Patent: WO2005/117904, 2005, A2. Location in patent: Page/Page column 463-464
[2] Patent: US5587388, 1996, A
[3] Patent: EP601486, 1994, A1
[4] Patent: US2006/223759, 2006, A1. Location in patent: Page/Page column 218
[5] Justus Liebigs Annalen der Chemie, 1959, vol. 624, p. 25,29