1,3-Dichloroacetone → HCID 57550208, compound

HRID 1716849Notes

Reaction equation

HRID 1716849 reaction equation
[N:1]1([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17](=[S:19])[NH2:18])=[CH:13][CH:12]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[Cl:20][CH2:21][C:22]([CH2:24]Cl)=O>C(O)C>[Cl:20][CH2:21][C:22]1[N:18]=[C:17]([C:14]2[CH:15]=[CH:16][C:11]([CH2:10][N:1]3[C:5]4[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=4[N:3]=[CH:2]3)=[CH:12][CH:13]=2)[S:19][CH:24]=1

Participants

4

Reactant 2

HCID 107931,3-DichloroacetoneHCID 24700409HCID 24700409, compound

Product 1

HCID 57550208HCID 57550208, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 4-(1H-benzimidazol-1-ylmethyl)benzenecarbo-thioamide (0.50 g, 1.87 mmol) in ethanol was treated with 1,3-dichloroacetone (0.235 g, 1.85 mmol), heated at reflux temperature for 3 h, allowed to cool to room temperature and filtered. The filtercake was washed with cold ethanol and dried under vacuum to afford the title compound in 60% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 4.85 (s, 2H), 5.67 (s, 2H), 7.34-7.35 (m, 2H), 7.48 (d, J=7.6 Hz, 2H), 7.64-7.65 (m, 1H), 7.74-7.76 (m, 1H), 7.80 (s, 1H), 7.92 (d, J=7.6 Hz, 2H), 8.94 (s, 1H). LCMS (ESI+) 340 (MH+).

Workup

  1. temperatureheated
  2. temperatureat reflux temperature for 3 h
  3. filtrationfiltered
  4. washThe filtercake was washed with cold ethanol
  5. customdried under vacuum

Sources & evidence

ORD record
ord-4416b17eab8d45e79452317a847504f7
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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