Phosgene → HCID 12478920, compound

HRID 652818Notes

Reaction equation

HRID 652818 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:5]=[CH:6][CH:7]=[C:8]([NH2:13])[C:9]=1[C:10]([OH:12])=[O:11].[C:14](Cl)(=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(Cl)(Cl)=O>ClCCCl.CN(C)C=O.O>[Cl:3][C:4]1[C:9]2[C:10](=[O:12])[O:11][C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:13][C:8]=2[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 4

HCID 6371Phosgene2×HCID 7412Benzoyl chloride2×HCID 14798Sodium HydroxideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 12478920HCID 12478920, compoundYield 111.6%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent2×

Conditions

Temperature
40 °C

Procedure

40 g of 50% strength aqueous sodium hydroxide solution are added to a stirred suspension of 85.8 g of 6-chloroanthranilic acid in 1,250 g of 1,2-dichloroethane in the course of 10 minutes at from 20° to 30° C. The salt suspension is freed from water by refluxing it for 1 hour in a water separator. Thereafter, 56.2 g of benzoyl chloride are added in the course of 40 minutes at from 25° to 35° C., and stirring is continued for a further 30 minutes. Under the same conditions, a further 14.1 g of benzoyl chloride are added in the course of 5 minutes, and stirring is continued for 55 minutes at 25° C. 0.2 g of dimethylformamide are added, after which 64 g of gaseous phosgene are passed into the stirred, refluxed mixture in the course of 11/2 hours, and excess phosgene is then expelled by blowing in nitrogen. The reaction mixture is cooled to 40° C., and extracted three times with water and once with a little concentrated sodium chloride solution. Evaporating down the organic phase, in the final stage at 140° C. and under 20 mbar, gives 115 g (89%) of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one of melting point 148°-152° C. According to HPLC and comparison with an analytical standard, the purity is 86%.

Workup

  1. stirringstirring
  2. waitis continued for 55 minutes at 25° C
  3. extractionextracted three times with water
  4. customEvaporating down the organic phase

Sources & evidence

ORD record
ord-e8538e70f57146c0983f8e725fc3e08d
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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