Water → 2,4-Dimethyl-7-[2-chloro-6-fluoro-4-(trifluoromethyl)phenoxy]-2H-1,4-benzoxazine-3(4H)-thione

HRID 847338Notes

Reaction equation

[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH3:12])[C:7](=[S:11])[CH:8]([CH3:10])[O:9][C:4]=2[CH:3]=1.[Cl:15][C:16]1[CH:17]=[C:18]([C:24]([F:27])([F:26])[F:25])[CH:19]=[C:20]([F:23])[C:21]=1F.C(=O)([O-])[O-].[K+].[K+].O>CS(C)=O>[Cl:15][C:16]1[CH:17]=[C:18]([C:24]([F:25])([F:26])[F:27])[CH:19]=[C:20]([F:23])[C:21]=1[O:1][C:2]1[CH:14]=[CH:13][C:5]2[N:6]([CH3:12])[C:7](=[S:11])[CH:8]([CH3:10])[O:9][C:4]=2[CH:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

First, 7-hydroxy-2,4-dimethyl-2H-1,4-benzoxazine-3 (4H)-thione (0.2 g) and 3-chloro-4,5-difluorotrifluoromethylbenzene (0.3 g) were dissolved in DMSO (5 ml), potassium carbonate (0.2 g) was added thereto, and the mixture was stirred at 80° C. for one hr. Water (10 ml) was added thereto to terminate the reaction, and the reaction mixture was extracted with ethyl acetate (20 ml×2), washed with water and a saturated saline solution and dried over anhydrous magnesium sulfate. The solvent was distilled off in vacuo, and the residue was purified by silica gel chromatography (developing solvent: n-hexane/ethyl acetate=5/1) to prepare the title compound (0.2 g) as a colorless crystal.

Workup

customto terminate
customthe reaction
extractionthe reaction mixture was extracted with ethyl acetate (20 ml×2)
washwashed with water
dry with materiala saturated saline solution and dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off in vacuo
customthe residue was purified by silica gel chromatography (developing solvent: n-hexane/ethyl acetate=5/1)
customto prepare the title compound (0.2 g) as a colorless crystal

Sources & evidence

ORD record: ord-34a1436dac084a26adfa6ac3f4714360
Source dataset: uspto-grants-1992_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05141551

Reaction notes

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