Dimethyl Sulfoxide → 2-(2-Methylsulfanylphenyl)-5-trifluoromethylbenzothiazole

HRID 923762Notes

Reaction equation

HRID 923762 reaction equation
Cl.[NH2:2][C:3]1[CH:8]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:6]=[CH:5][C:4]=1[SH:13].[CH3:14][S:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[CH:18]=O.C(N(C(C)C)CC)(C)C.CS(C)=O>O>[CH3:14][S:15][C:16]1[CH:23]=[CH:22][CH:21]=[CH:20][C:17]=1[C:18]1[S:13][C:4]2[CH:5]=[CH:6][C:7]([C:9]([F:10])([F:11])[F:12])=[CH:8][C:3]=2[N:2]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 2864432-(Methylthio)benzaldehydeHCID 27346782-Amino-4-(trifluoromethyl)benzenethiol hydrochloride

Product 1

HCID 679811962-(2-Methylsulfanylphenyl)-5-trifluoromethylbenzothiazoleYield 59.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
175 °C

Procedure

A mixture of 2-amino-4-trifluoromethylbenzenethiol hydrochloride (0.50 g), 2-methylsulfanylbenzaldehyde (0.33 g), diisopropylethylamine (0.28 g), and DMSO (4 ml) was heated to 170-180° C., and stirred with heating for 3 hours. Into the reaction mixture cooled to room temperature, water was poured, and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography to give 0.42 g of 2-(2-methylsulfanylphenyl)-5-trifluoromethylbenzothiazole (hereinafter referred to as Present Compound 84).

Workup

  1. temperaturewith heating for 3 hours
  2. temperatureInto the reaction mixture cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water and saturated brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5067de8eff1c44d6959885cb977f3073
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

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