Benzoyl chloride, 3-chloro- → 2-(3-Chlorophenyl)-6-methyl-4H-3,1-benzoxazin-4-one

Reaction equation

[CH3:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=[O:8])[C:5]([NH2:11])=[CH:4][CH:3]=1.[Cl:12][C:13]1[CH:14]=[C:15]([CH:19]=[CH:20][CH:21]=1)[C:16](Cl)=O>>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:16]([C:15]3[CH:19]=[CH:20][CH:21]=[C:13]([Cl:12])[CH:14]=3)[O:8][C:7](=[O:9])[C:6]=2[CH:10]=1

Participants

Reactant 2

HCID 69252Benzoyl chloride, 3-chloro-

HCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 3170802-(3-Chlorophenyl)-6-methyl-4H-3,1-benzoxazin-4-oneYield 91.1%

Procedure

When the reaction conditions of Example 1 are employed but 11.3 g of 5-methylanthranilic acid and 13.1 g of 3-chlorobenzoyl chloride are used, 18.5 g (91%) of 6-methyl-2-(m-chlorophenyl)-4H-3,1-benzoxazin-4-one of melting point 160°-162° C. are obtained.

Workup

customWhen the reaction conditions of Example 1

Sources & evidence

ORD record: ord-58edeff5b5eb461c9becc0d5c12e6111
Source dataset: uspto-grants-1987_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04673740

Reaction notes

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