Sodium Hydroxide → HCID 13690507, compound

HRID 652816Notes

Reaction equation

[F:1][C:2]([S:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](F)=[O:11])=[CH:8][CH:7]=1)([F:4])[F:3].[OH-].[Na+].[Cl:17][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([NH2:27])[C:23]=1[C:24](O)=[O:25]>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.ClCCCl>[Cl:17][C:18]1[C:23]2[C:24](=[O:25])[O:11][C:10]([C:9]3[CH:13]=[CH:14][C:6]([S:5][C:2]([F:4])([F:3])[F:1])=[CH:7][CH:8]=3)=[N:27][C:22]=2[CH:21]=[CH:20][CH:19]=1

Participants

Conditions

Temperature: 30 °C

Procedure

33.6 g of 4-trifluoromethylmercaptobenzoyl fluoride and 12 g of 50% strength sodium hydroxide solution are added simultaneously via 2 feed apparatuses in the course of 30 minutes at from 20° to 39° C. to a stirred mixture of 25.7 g of 6-chloroanthranilic acid, 0.27 g of benzyltrimethylammonium chloride and 450 g of 1,2-dichloroethane. Stirring is continued for 90 minutes at 27° C., after which the water is separated off and 21.5 g of phosphoryl chloride are added at 70° C. Stirring is continued for 3 hours at 82° C., after which the mixture is cooled to 30° C. and extracted 3 times with water. Evaporating down the solution, in the final stage at 140° C. and under 2 mbar, gives 48.8 g (91%) of 5-chloro-2-(p-trifluoromethylmercaptophenyl)-4H-3,1-benzoxazin-4-one of melting point 135°-140° C.

Workup

customafter which the water is separated off
addition21.5 g of phosphoryl chloride are added at 70° C
stirringStirring
waitis continued for 3 hours at 82° C.
extractionextracted 3 times with water
customEvaporating down the solution

Sources & evidence

ORD record: ord-a8f469e9a385426a913ea6a9f66a537f
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04673740

Reaction notes

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