Hexamethyldisilazane → Ethyl 1-cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylate

HRID 8893

Reaction equation

HRID 8893 reaction equation
S([O-])([O-])(=O)=O.[NH4+].[NH4+].[CH2:8]([O:10][C:11](=[O:23])[C:12]([NH:19][C:20](=O)[CH3:21])=[C:13]([NH:15][CH:16]1[CH2:18][CH2:17]1)[CH3:14])[CH3:9].C[Si](C)(C)N[Si](C)(C)C>>[CH2:8]([O:10][C:11]([C:12]1[N:19]=[C:20]([CH3:21])[N:15]([CH:16]2[CH2:18][CH2:17]2)[C:13]=1[CH3:14])=[O:23])[CH3:9]

Participants

4

Reactant 3

HCID 13838HexamethyldisilazaneHCID 6097028Ammonium SulfateHCID 692908002-Acetylamino-3-cyclopropylamino-but-2-enoic acid ethyl ester

Product 1

HCID 45097089Ethyl 1-cyclopropyl-2,5-dimethyl-1H-imidazole-4-carboxylate

Conditions

Temperature
145 °C

Procedure

Fine powdered ammonium sulfate (0.13 g, 1 mmol) was added to a suspension of Z)-2-acetylamino-3-cyclopropylamino-but-2-enoic acid ethyl ester (7.0 g, 20 mmol) and hexamethyldisilazane (50 ml, 235 mmol) and refluxed over night at 145° C. The reaction mixture was evaporated and extracted with ethyl acetate and water. The organic phase was dried over sodium sulfate and evaporated. The crude product was purified by column chromatography on silica gel (ethyl acetate/methanol 4:1) and the desired compound was obtained as a light brown solid (1.3 g, 31%), MS: m/e=209.1 (M+H+).

Workup

  1. customThe reaction mixture was evaporated
  2. extractionextracted with ethyl acetate and water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe crude product was purified by column chromatography on silica gel (ethyl acetate/methanol 4:1)

Sources & evidence

ORD record
ord-ac2fb617a7cc49e7926340e6ef4fdd34
Source dataset
uspto-grants-2006_08
Patent number
US07091222B2

Linked notes

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