Benzoyl chloride → HCID 12478920, compound

HRID 652810Notes

Reaction equation

HRID 652810 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].S(Cl)(Cl)=O>[Cl-].C[N+](C)(C)CC1C=CC=CC=1.O.ClCCCl>[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

8

Reactant 4

HCID 7412Benzoyl chlorideHCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 12478920HCID 12478920, compoundYield 98%

Reagents, catalysts & solvents 3

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolventHCID 962WaterSolvent

Conditions

Temperature
40 °C

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 23° to 42° C. to a stirred mixture of 85.8 g of finely divided 6-chloroanthranilic acid, 0.9 g of trimethylbenzylammonium chloride and 1,250 g of 1,2-dichloroethane. Stirring is continued for 90 minutes at 28° C., the mixture is refluxed for 1 hour with separation of water, and 63.1 parts of thionyl chloride are added in the course of 45 minutes at 70° C., while stirring. Stirring is continued for 90 minutes at 82° C., after which the mixture is cooled to 40° C., extracted 3 times with water and evaporated down under reduced pressure, in the final stage at 140° C. under 20 mbar, to give 126.2 g (98%) of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one of melting point 151°-153° C. Comparison with a purified standard using HPLC shows that the purity is 96%.

Workup

  1. additionare added in the course of 45 minutes at 70° C.
  2. stirringwhile stirring
  3. stirringStirring
  4. waitis continued for 90 minutes at 82° C.
  5. extractionextracted 3 times with water
  6. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-f8b73d417bcf49a189827d43027698ba
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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