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

HRID 533622Notes

Reaction equation

HRID 533622 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-afbde1cc523044a9a107c21700f75c2a
Source dataset
uspto-grants-2014_10
Patent number
US08853238B2

Reaction notes

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