1,3-Dichloroacetone → HCID 68542644, compound

HRID 1441272Notes

Reaction equation

HRID 1441272 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18](=[S:20])[NH2:19].[Cl:21][CH2:22][C:23]([CH2:25]Cl)=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:13][CH2:14][O:15][CH2:16][CH2:17]1)[CH:8]=[C:7]2[C:18]1[S:20][CH:25]=[C:23]([CH2:22][Cl:21])[N:19]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 86622680HCID 86622680, compound

Product 1

HCID 68542644HCID 68542644, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carbothioic acid amide (920 mg, 3.0 mmol), 1,3-dichloroacetone (571 mg, 4.50 mmol) in toluene (30 ml) was stirred at 40° C. for 18 h. The reaction mixture was concentrated in vacuo, and the obtained crystals were washed with 10% dichloromethane (v/v) in n-heptane to give 7-chloro-3-[4-(chloromethyl)-[1,3]-thiazol-2-yl]-1-(tetrahydropyran-4-yl)methyl-1H-indole (590 mg, 1.5 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. washthe obtained crystals were washed with 10% dichloromethane (v/v) in n-heptane

Sources & evidence

ORD record
ord-f75a8de4fd514b5bb6fdf4679c63775e
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

Loading…