Diethylamine → HCID 54567558, compound

HRID 1606045Notes

Reaction equation

HRID 1606045 reaction equation
Cl[CH2:2][C:3]1[N:4]([C:8]2[S:9][C:10]([CH2:22][CH3:23])=[CH:11][C:12]=2[C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[CH:5]=[CH:6][N:7]=1.[CH2:24]([NH:26][CH2:27][CH3:28])[CH3:25]>C(O)C>[CH2:24]([N:26]([CH2:2][C:3]1[N:4]([C:8]2[S:9][C:10]([CH2:22][CH3:23])=[CH:11][C:12]=2[C:13](=[O:21])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[CH:5]=[CH:6][N:7]=1)[CH2:27][CH3:28])[CH3:25]

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 13218676HCID 13218676, compound

Product 1

HCID 54567558HCID 54567558, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5.6 g of 2-chloromethyl-1-(3o-chlorobenzoyl-5-ethyl-2-thienyl)imidazole in 50 ml of ethanol is added 4 g of diethylamine, and the mixture is stirred at 50°C for 2 hours. After allowing the mixture to stand overnight, the solvent is distilled off under reduced pressure. The residue to which a water is added is extracted with ethyl acetate. The extract is washed with water and dried over anhydrous magnesium sulfate. The solvent is distilled off under reduced pressure. The residual brown oil is chromatographed on 150 g of 70 - 325 mesh silica gel with chloroform as eluent. The eluates are combined and concentrated in vacuo to give 2-diethylaminomethyl-1-(3-o-chlorobenzoyl-5-ethyl-2-thienyl)imidazole as yellowish transparent oil (nD21 = 1.5813).

Workup

  1. waitto stand overnight
  2. distillationthe solvent is distilled off under reduced pressure
  3. additionThe residue to which a water is added
  4. extractionis extracted with ethyl acetate
  5. washThe extract is washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent is distilled off under reduced pressure
  8. customThe residual brown oil is chromatographed on 150 g of 70 - 325 mesh silica gel with chloroform as eluent
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d9ef3515f713474c93feed3e1f95b5a3
Source dataset
uspto-grants-1976_04
Patent number
US03952006

Reaction notes

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