Water → HCID 117974495, compound

HRID 2272917Notes

Reaction equation

HRID 2272917 reaction equation
[H-].[Na+].Br[C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[S:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:12]=2[N:13]=1.[CH2:22]([SH:24])[CH3:23].O>CN1C(=O)CCC1>[CH2:22]([S:24][C:4]1[CH:8]=[CH:7][S:6][C:5]=1[C:9]1[S:10][C:11]2[CH:17]=[CH:16][C:15]([C:18]([F:21])([F:20])[F:19])=[CH:14][C:12]=2[N:13]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 117974258HCID 117974258, compound

Product 1

HCID 117974495HCID 117974495, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

0.11 g of sodium hydride (60%) was added to a solution of 0.65 g of 2-(3-bromothiophen-2-yl)-5-(trifluoromethyl)benzothiazole and 0.15 ml of ethanethiol in NMP 6 ml 0° C., and the mixture was stirred at room temperature for 1 hour. Water was poured into the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with a 10% aqueous hydrochloric acid solution and a saturated aqueous salt solution and dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The resulting residue was applied to a silica gel column chromatography to obtain 0.61 g of 2-(3-ethylthiothiophen-2-yl)-5-(trifluoromethyl)benzothiazole (Compound of Present Invention (37)).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with a 10% aqueous hydrochloric acid solution
  3. dry with materiala saturated aqueous salt solution and dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bba1eb75b11f4a08a7f4aa9a91a1e333
Source dataset
uspto-grants-2015_09
Patent number
US09120792B2

Reaction notes

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