Benzoyl chloride → HCID 12478920, compound

HRID 652817Notes

Reaction equation

HRID 652817 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]>[Cl-].C[N+](C)(C)CC1C=CC=CC=1.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

6

Reactant 3

HCID 7412Benzoyl chloride2×HCID 14798Sodium Hydroxide2×HCID 750712-Amino-6-chlorobenzoic acid

Product 1

HCID 12478920HCID 12478920, compoundYield 112.6%

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolvent

Conditions

Temperature
40 °C

Procedure

92.3 g of benzoyl chloride and 52.6 g of 50% strength aqueous sodium hydroxide solution are introduced simultaneously via 2 feed apparatuses in the course of 40 minutes at from 22° to 38° C. to a stirred suspension of 128.6 g of 6-chloroanthranilic acid and 1.35 g of trimethylbenzylammonium chloride in 1,870 g of 1,2-dichloroethane. Stirring is continued for 30 minutes at 32° C., after which a further 16.3 g of benzoyl chloride and 9.3 g of 50% strength sodium hydroxide solution, as described above, are added in the course of 5 minutes, and the mixture is stirred for a further 55 minutes at from 25° to 30° C. The mixture is then refluxed for 11/4 hours to separate off water, this procedure being continued until the organic phase in the water separator no longer appears cloudy. 0.2 g of dimethylformamide are added, after which 96 g of gaseous phosgene are passed into the stirred refluxed mixture in the course of 13/4 hours, and excess phosgene is then expelled in the course of 5 minutes by blowing in nitrogen. After cooling to 40° C., the reaction mixture is extracted 3 times with water and once with a little concentrated sodium chloride solution. The organic phase is evaporated down under reduced pressure, in the final stage at 140° C. and under 20 mbar, 190.5 g (98.6%) of 5-chloro-2-phenyl-4H-3,1-benzoxazin-4-one of melting point 153°-156° C. being obtained. The purity according to HPLC is 97.4%.

Workup

  1. additionare added in the course of 5 minutes
  2. stirringthe mixture is stirred for a further 55 minutes at from 25° to 30° C
  3. temperatureThe mixture is then refluxed for 11/4 hours
  4. customto separate off water
  5. addition0.2 g of dimethylformamide are added
  6. temperaturerefluxed mixture in the course of 13/4 hours, and excess phosgene
  7. customis then expelled in the course of 5 minutes
  8. extractionthe reaction mixture is extracted 3 times with water
  9. customThe organic phase is evaporated down under reduced pressure

Sources & evidence

ORD record
ord-0a1b3cdea3bd4a2bbda757238871e8d7
Source dataset
uspto-grants-1987_06
Patent number
US04673740

Reaction notes

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