Dimethylformamide → 2-Chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloride

HRID 2167425Notes

Reaction equation

S(Cl)([Cl:3])=O.[Cl:5][C:6]1[C:14]([C:15]2[CH2:19][CH2:18][O:17][N:16]=2)=[C:13]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=[CH:11][C:7]=1[C:8](O)=[O:9].CN(C)C=O>C1(C)C=CC=CC=1>[Cl:5][C:6]1[C:14]([C:15]2[CH2:19][CH2:18][O:17][N:16]=2)=[C:13]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:12]=[CH:11][C:7]=1[C:8]([Cl:3])=[O:9]

Participants

Conditions

Temperature: 110 °C

Procedure

74.8 g (0.63 mol) of thionyl chloride in 50 ml of dry toluene were added dropwise at 50° C. to a solution of 139.0 g of 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoic acid, 1 ml of dimethylformamide and 1 l of dry toluene. After the mixture had been heated for 6 hours at 110° C., the solvent was distilled off. This gave 2-chloro-3-(4,5-dihydroisoxazol-3-yl)-4-methylsulfonylbenzoyl chloride in quantitative yield.

Workup

distillationthe solvent was distilled off

Sources & evidence

ORD record: ord-c1a76729ea9741e986369771a82df892
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045465B1

Reaction notes

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