Benzoyl chloride → HCID 12478920, compound

HRID 652811Notes

Reaction equation

HRID 652811 reaction equation
[C:1](Cl)(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[Cl:12][C:13]1[CH:14]=[CH:15][CH:16]=[C:17]([NH2:22])[C:18]=1[C:19]([OH:21])=[O:20]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O.ClC1C=CC=CC=1Cl>[Cl:12][C:13]1[C:18]2[C:19](=[O:21])[O:20][C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[N:22][C:17]=2[CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 12478920HCID 12478920, compoundYield 94%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 67553Tetrabutylammonium IodideCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

70.3 g of benzoyl chloride and 40 g of 50% strength aqueous sodium hydroxide solution are added simultaneously via 2 feed apparatuses in the course of 40 minutes at from 20° to 35° C. to a stirred mixture of 85.8 g of 6-chloroanthranilic acid, 1.3 g of tetrabutylammonium iodide, 0.5 g of dimethylformamide and 1,300 g of 1,2-dichlorobenzene. Stirring is continued for 90 minutes at 30° C., the water is separated off at from 75° to 90° C. and under from 20 to 50 mbar and 64 g of phosgene are added via a gas inlet tube in the course of 1 hour at from 100° to 105° C., while stirring. The mixture is cooled to room temperature while nitrogen is passed through, after which insoluble substances are filtered off and the filtrate is evaporated down, in the final stage at 140° C. and under 20 mbar. Distillation at 221°-230° C. and under 4-5 mbar gives 121 g (94%) of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one of melting point 155°-157° C. The product is 99.5% pure according to HPLC.

Workup

  1. customthe water is separated off at from 75° to 90° C. and under from 20 to 50 mbar and 64 g of phosgene
  2. additionare added via a gas inlet tube in the course of 1 hour at from 100° to 105° C.
  3. stirringwhile stirring
  4. filtrationare filtered off
  5. customthe filtrate is evaporated down
  6. customat 140° C.
  7. distillationDistillation at 221°-230° C.

Sources & evidence

ORD record
ord-a10fe2012fcf43f38c14cc5c6b409401
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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