Imidazole → HCID 19857288, compound

HRID 2073507Notes

Reaction equation

HRID 2073507 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.S(Cl)(Cl)=O.[CH3:10][C:11]1[S:12][C:13]([C:17](O)=[O:18])=[C:14]([CH3:16])[N:15]=1>O1CCCC1>[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:17]([C:13]1[S:12][C:11]([CH3:10])=[N:15][C:14]=1[CH3:16])=[O:18]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24386Thionyl ChlorideHCID 736488Dimethyl-1,3-thiazole-5-carboxylic acid

Product 1

HCID 19857288HCID 19857288, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of imidazole (2.72 g; 40 mmol) in dry tetrahydrofuran (60 ml) was added dropwise thionyl chloride (1.20 g; 10 mmol) under ice-cooling while stirring. After the resultant mixture was turned to room temperature, 2,4-dimethyl-5-thiazolecarboxylic acid (1.57 g; 10 mmol) was added thereto at once, and stirring was continued for 30 minutes, whereby 5-imidazolylcarbonyl-2,4-dimethylthiazole was produced. To the mixture was added dropwise a solution of 2-(2-furyl)aminoacetonitrile (1.46 g; 12 mmol) in dry tetrahydrofuran under ice-cooling, and the resultant mixture was stirred at room temperature for 1 hour. After completion of the reaction, tetrahydrofuran was removed under reduced pressure to separate the residue. Water was added to the residue, which was extracted with ethyl acetate. The ethyl acetate layer was washed twice with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give crude crystals. Recrystallization from ethanol gave 2.0 g of 2-(2,4-dimethylthiazole-5-carboxamido)-2-(2-furyl)acetonitrile as colorless crystals. m.p., 108° -109° C. Yield, 74%.

Workup

  1. temperaturecooling
  2. customwas turned to room temperature
  3. stirringat once, and stirring

Sources & evidence

ORD record
ord-40dbde0a07c943f79af71d4e54b52386
Source dataset
uspto-grants-1990_04
Patent number
US04918089

Reaction notes

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