2-Chlorocyclohexanone → HCID 11666453, compound

HRID 1819746Notes

Reaction equation

HRID 1819746 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([SH:12])[NH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][C:15]1=O>C(O)CCC>[ClH:13].[C:1]1([C:7]2[N:8]3[C:9]([S:12][C:14]4[CH2:19][CH2:18][CH2:17][CH2:16][C:15]=43)=[N:10][CH:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 132032-ChlorocyclohexanoneHCID 178527829HCID 178527829, compound

Product 1

HCID 11666453HCID 11666453, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of 4-Phenyl-1H-imidazole-2-thiol 24 (Maeda et al., Chem. Pharm. Bull. 1984, 32, 2536-2543) and 2-chlorocyclohexanone was refluxed in butanol for 3 hours. After cooling, the resulting precipitate was filtered to give 25 in 75% yield: mp 274-278° C.; 1H-NMR (DMSO-d6) 1.89 (m, 4H), 2.76 (m, 4H), 7.38 (t, 1H), 7.49 (t, 2H), 7.88 (d, 2H), 8.51 (s, 1H); HR-MS (EI) m/z 254.0874 (M+).

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was filtered

Sources & evidence

ORD record
ord-11dc59f316374e8c94fbf99186ed16eb
Source dataset
uspto-grants-2009_10
Patent number
US07601846B2

Reaction notes

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