1,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzene → tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

HRID 1522769Notes

Reaction equation

HRID 1522769 reaction equation
[CH3:1][C:2]1[CH:14]=[C:13]([C:15]2OC(=O)[S:17][N:16]=2)[CH:12]=[CH:11][C:3]=1[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5].[Cl:21][C:22]1[CH:27]=[C:26]([C:28]([C:30]([F:33])([F:32])[F:31])=[CH2:29])[CH:25]=[C:24]([Cl:34])[CH:23]=1>>[Cl:21][C:22]1[CH:27]=[C:26]([C:28]2([C:30]([F:31])([F:32])[F:33])[S:17][N:16]=[C:15]([C:13]3[CH:12]=[CH:11][C:3]([C:4]([O:6][C:7]([CH3:8])([CH3:9])[CH3:10])=[O:5])=[C:2]([CH3:1])[CH:14]=3)[CH2:29]2)[CH:25]=[C:24]([Cl:34])[CH:23]=1

Participants

3

Reactant 2

HCID 231598231,3-Dichloro-5-(3,3,3-trifluoroprop-1-en-2-yl)benzeneHCID 89445353Tert-butyl 2-methyl-4-(2-oxo-1,3,4-oxathiazol-5-yl)benzoate

Product 1

HCID 89444266tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate

Procedure

A solution of tert-butyl 2-methyl-4-(2-oxo-1,3,4-oxathiazol-5-yl)benzoate (50 mg) in 1,3-dichloro-5-[1-(trifluoromethyl)vinyl]benzene (5 mL, prepared according to WO 2005085216) was heated 190° C. during 10 minutes in a microwave. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) then on preparative HPLC to give tert-butyl 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4H-isothiazol-3-yl]-2-methyl-benzoate (18.5 mg) as a solid. 1H-NMR (CDCl3, 400 MHz): δ=7.86 (d, 1 H), 7.54-7.64 (m, 2 H), 7.41 (t, 1 H), 7.31 (s, 2 H), 4.23 (d, 1 H), 3.88 (d, 1 H), 2.61 (s, 3 H), 1.61 ppm (s, 9 H).

Workup

  1. customThe residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate)

Sources & evidence

ORD record
ord-cd72ed6d177a49ae8ee82b52bbdd4cdb
Source dataset
uspto-grants-2015_07
Patent number
US09078444B2

Reaction notes

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