MORPHOLINE-4-SULFONYL CHLORIDE Chemical Properties

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 Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26

RIDADR 

UN3265

HazardClass 

IRRITANT

MORPHOLINE-4-SULFONYL CHLORIDE Usage And Synthesis

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

MORPHOLINE-4-SULFONYL CHLORIDE(1828-66-6)Related Product Information

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• Methyl Morpholine-3-carboxylate-HCl
• 2-Morpholinecarboxylicacid,methylester(9CI)
• methyl morpholine-2-carboxylate hydrochloride
• MORFOLINE METHYLCARBAMATE
• Nifedipine
• 4-Chlorosulfonylimidazole
• 1-N-BOC-MORPHOLINE
• Dimethylsulfamoyl chloride
• METHYLSULFAMOYL CHLORIDE
• 2-methylmorpholine-4-sulfonyl chloride
• DIETHYLSULFAMOYL CHLORIDE
• 2,6-DIMETHYLMORPHOLINE-4-SULFONYL CHLORIDE
• MORPHOLINE-4-SULFONYL CHLORIDE