Dimethylformamide dimethyl acetal → 5-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-one

HRID 2113989Notes

Reaction equation

HRID 2113989 reaction equation
[C:1]([C:4]1[S:8][C:7](=[O:9])[N:6]([CH3:10])[C:5]=1[CH3:11])(=[O:3])[CH3:2].CO[CH:14](OC)[N:15]([CH3:17])[CH3:16]>>[CH3:14][N:15]([CH3:17])[CH:16]=[CH:2][C:1]([C:4]1[S:8][C:7](=[O:9])[N:6]([CH3:10])[C:5]=1[CH3:11])=[O:3]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 672693935-acetyl-3,4-dimethyl-3H-thiazol-2-one

Product 1

HCID 672693735-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-oneYield 44.5%

Conditions

Temperature
100 °C

Procedure

5-Acetyl-3,4-dimethyl-3H-thiazol-2-one (4.64 g, 27.10 mmol) and dimethylformamide dimethyl acetal (8.4 mL, 59.62 mmol) were mixed in a dry, argon-flushed flask, and heated at 100° C. for 3 h. The mixture was cooled, producing some precipitation, which was enhanced by the addition of an equal volume of Et2O. The resulting orange solid was filtered and washed with Et2O to give 2.73g of 5-(3-dimethylamino-acryloyl)-3,4-dimethyl-3H-thiazol-2-one. 1H-NMR (d6-DMSO): δ 2.52 (s, 3H), 2.82 (bs, 3H), 3.11 (bs, 3H), 3.22 (s, 3H), 5.10 (d, 1H, J=12.2 Hz), 7.61 (d, 1H, J=11.7 Hz). IR (ATR): 1669 and 1630 cm−1 (CO str).

Workup

  1. customflushed flask
  2. temperatureThe mixture was cooled
  3. customproducing
  4. customsome precipitation, which
  5. additionwas enhanced by the addition of an equal volume of Et2O
  6. filtrationThe resulting orange solid was filtered
  7. washwashed with Et2O

Sources & evidence

ORD record
ord-418ea53bdd864cfaaaecf3a4e07793d5
Source dataset
uspto-grants-2008_10
Patent number
US07432260B2

Reaction notes

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