5-Chloroisatoic anhydride Chemical Properties

Melting point:

300 °C (dec.) (lit.)

Density 

1.540±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly)

form 

Solid

pka

9.76±0.20(Predicted)

color 

Off-White

CAS DataBase Reference

4743-17-3(CAS DataBase Reference)

EPA Substance Registry System

2H-3,1-Benzoxazine-2,4(1H)-dione, 6-chloro- (4743-17-3)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-37/39

WGK Germany 

3

Hazard Note 

Irritant

HS Code 

2934999090

MSDS

• Language:English Provider:SigmaAldrich

5-Chloroisatoic anhydride Usage And Synthesis

Chemical Properties

White powder

Uses

5-Chloroisatoic Anhydride was used as a reagent in the synthesis of 2-acetamidobenzamides bearing the 2-phenoxy functionality which display antiproliferative activity against certain tumor cell lines. Also used in the preparation of inhibitors of delta-5 desaturase.

Preparation

5-Chloroisatoic anhydride is prepared from 5-chloro indole (9c) by stirring in a 4:1 mixture of DMF/H2O for 16 h at room temperature.
¹ H NMR (DMSO-d6): δ 11.85 (s, br., 1H), 7.96 (dd, J = 0.8, 8.7 Hz, 1H), 7.87 (dd, J = 2.3, 8.7 Hz, 1H), 7.09 (dd, J = 8.8, 0.8 Hz, 1H).

Synthesis

Step 1 Synthesis of 6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione: 2-Amino-5-chlorobenzoic acid (17 g, 0.1 mol) and 1,2-dichloroethane (200 mL) were added to a 500 mL three-necked round-bottom flask. A solution of triphosgene (21 g, 0.21 mol) in 1,2-dichloroethane (100 mL) was slowly added dropwise to the above solution at 80 °C. After the dropwise addition was completed, the reaction mixture was continued to be heated and stirred at 80°C for 3 hours. After completion of the reaction, the mixture was cooled to room temperature in an ice water bath. The precipitated white solid precipitate was collected by filtration and washed with an appropriate solvent and dried to afford 6-chloro-1H-benzo[d][1,3]oxazine-2,4-dione (19 g, 97% yield). The product was characterized by 1H NMR (300 MHz, DMSO-d6): δ 11.85 (br, 1H), 7.88 (d, J = 2.4 Hz, 1H), 7.78 (dd, J = 8.7, 2.4 Hz, 1H), 7.15 (d, J = 8.7 Hz, 1H).

References

[1] Patent: US2010/120741, 2010, A1. Location in patent: Page/Page column 78
[2] Patent: WO2011/112731, 2011, A2. Location in patent: Page/Page column 174
[3] Journal of Medicinal Chemistry, 2013, vol. 56, # 16, p. 6434 - 6456
[4] Chemical Biology and Drug Design, 2010, vol. 75, # 5, p. 444 - 454
[5] Bioorganic and Medicinal Chemistry Letters, 2014, vol. 24, # 10, p. 2295 - 2299

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