Diketene → HCID 21283676, compound

HRID 2232379Notes

Reaction equation

HRID 2232379 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:8])=[C:5]([CH3:7])[N:6]=1.[CH2:9]=[C:10]1[O:14][C:12](=[O:13])[CH2:11]1>C1(C)C=CC=CC=1>[CH3:7][C:5]1[N:6]=[C:2]([NH:1][C:12](=[O:13])[CH2:11][C:10](=[O:14])[CH3:9])[S:3][C:4]=1[CH3:8]

Participants

4

Reactant 2

HCID 12661DiketeneHCID 732382-Amino-4,5-dimethyl-1,3-thiazole

Product 1

HCID 21283676HCID 21283676, compoundYield 38.6%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-amino-4,5-dimethylthiazole (0.05 mole) in toluene (30 ml), cooled in ice was added diketene (0.05 mole) at such a rate that the temperature did not rise above 20° C. When addition was complete the mixture was stirred at room temperature for 2 hours and evaporated to dryness to give N-(4,5-dimethylthiazol-2-yl)-3-ketobutanamide (4.1 g), Rf (silica; diethylamine/ethyl acetate 1:19) 0.47; m.p. 191°-3° C.

Workup

  1. customdid not rise above 20° C
  2. additionWhen addition
  3. customevaporated to dryness

Sources & evidence

ORD record
ord-600ce5e98f304059a2107cefb5be3de6
Source dataset
uspto-grants-1988_11
Patent number
US04788205

Reaction notes

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