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

Reaction equation

[C:1]([C:4]1[S:8][C:7]([CH3:9])=[N:6][C:5]=1[CH3:10])(=O)[CH3:2].C[O:12][CH:13](OC)[N:14]([CH3:16])[CH3:15]>>[CH3:10][C:5]1[N:6]=[C:7]([CH3:9])[S:8][C:4]=1/[CH:1]=[CH:2]/[C:13]([N:14]([CH3:16])[CH3:15])=[O:12]

Participants

Reactant 2

HCID 78373Dimethylformamide dimethyl acetal

HCID 5208882,4-Dimethyl-5-acetylthiazole

Product 1

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

Procedure

A solution of 5-acetyl-2,4-dimethylthiazole (10 g, 60 mmol) in N,N-dimethylformamide dimethylacetal (10 mL) was refluxed under N2. After 18 h, the reaction mixture was evaporated to dryness and the residue was recrystallised from iPr2O/CH2Cl2 to afford the title compound as a brown powder (9.94 g, 79%). 1H-NMR (300 MHz, CDCl3) δ2.66 (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

customthe reaction mixture was evaporated to dryness
customthe residue was recrystallised from iPr2O/CH2Cl2

Sources & evidence

ORD record: ord-956af8e832b341b9a97d2cec1966f362
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699854B2

Reaction notes

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