Dimethylformamide dimethyl acetal → 3-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone

HRID 32358

Reaction equation

HRID 32358 reaction equation
[CH3:1][C:2]1[S:3][C:4]([C:8](=O)[CH3:9])=[C:5]([CH3:7])[N:6]=1.C[O:12][CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:7][C:5]1[N:6]=[C:2]([CH3:1])[S:3][C:4]=1/[CH:8]=[CH:9]/[C:13]([N:14]([CH3:16])[CH3:15])=[O:12]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 5208882,4-Dimethyl-5-acetylthiazole

Product 1

HCID 916216443-Dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenoneYield 79%

Procedure

A solution of 1-(2,4-dimethyl-thiazol-5-yl)-ethanone (10 g, 0.06 mol) in of N,N-dimethylformamide dimethylacetal (10 mL) was refluxed under N2. After 18 h, the reaction mixture was evaporated to dryness in vacuo. The resulting solid material was crystallised from a minimum amount of isopropyl ether/CH2Cl2 to afford 9.94 g 3-dimethylamino-1-(2,4-dimethyl-thiazol-5-yl)-propenone as a brown powder (79%). 1H-NMR (CDCl3) δ: 2.66 (s, 6H, CH3), 2.70 (s, 6H, CH3), 5.37 (d, 1H, J=12.2 Hz, CH), 7.66 (d, 1H, J=12.2 Hz, CH).

Workup

  1. customthe reaction mixture was evaporated to dryness in vacuo
  2. customThe resulting solid material was crystallised from a minimum amount of isopropyl ether/CH2Cl2

Sources & evidence

ORD record
ord-0dc93e9cec304d439f82e2a85f159a06
Source dataset
uspto-grants-2008_09
Patent number
US07427627B2

Linked notes

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