1-Chlorobutane-2,3-dione → HCID 68695579, compound

HRID 644039Notes

Reaction equation

HRID 644039 reaction equation
Cl[CH2:2][C:3](=O)[C:4](=[O:6])[CH3:5].[CH:8]1([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][CH3:25])[C:17]([C:26](=[S:28])[NH2:27])=[CH:16]2)[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1>C(O)C>[CH:8]1([CH2:14][N:15]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][C:22]=3[O:24][CH3:25])[C:17]([C:26]3[S:28][CH:2]=[C:3]([C:4](=[O:6])[CH3:5])[N:27]=3)=[CH:16]2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

4

Reactant 2

HCID 796801-Chlorobutane-2,3-dioneHCID 86073268HCID 86073268, compound

Product 1

HCID 68695579HCID 68695579, compoundYield 75.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 1-chloro-2,3-butanedione (0.717 g, 5.95 mmol) in ethanol (3 ml) was added dropwise to a solution of 1-(cyclohexyl)methyl-7-methoxy-1H-indole-3-carbothioic acid amide (prepared as in Example 16; 1.20 g, 3.97 mmol) in ethanol (12 ml) at room temperature, and then the resulting mixture was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and the obtained residue was mixed with dichloromethane (50 ml) and washed sequentially with water and brine, dried over magnesium sulfate and concentrated in vacuo. The obtained residue was purified by column chromatography eluting with 33% (v/v) ethyl acetate in n-heptane to afford 1-{2-[1-(cyclohexyl)methyl-7-methoxy-1H-indol-3-yl]thiazol-4-yl}ethanone as a brown solid (1.11 g).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. additionthe obtained residue was mixed with dichloromethane (50 ml)
  3. washwashed sequentially with water and brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe obtained residue was purified by column chromatography
  7. washeluting with 33% (v/v) ethyl acetate in n-heptane

Sources & evidence

ORD record
ord-c14c02b4e34441b692760fa5c8747f6c
Source dataset
uspto-grants-2010_04
Patent number
US07700634B2

Reaction notes

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