Dimethylamine → 5-[4-(Dimethylamino)benzoyl]-4-methyl-1,3-thiazol-2(3H)-one

HRID 569786Notes

Reaction equation

HRID 569786 reaction equation
[CH3:1][NH:2][CH3:3].F[C:5]1[CH:19]=[CH:18][C:8]([C:9]([C:11]2[S:15][C:14](=[O:16])[NH:13][C:12]=2[CH3:17])=[O:10])=[CH:7][CH:6]=1>C(O)C>[CH3:1][N:2]([CH3:3])[C:5]1[CH:19]=[CH:18][C:8]([C:9]([C:11]2[S:15][C:14](=[O:16])[NH:13][C:12]=2[CH3:17])=[O:10])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 674DimethylamineHCID 141522585-(4-Fluorobenzoyl)-4-methyl-1,3-thiazol-2(3H)-one

Product 1

HCID 141522595-[4-(Dimethylamino)benzoyl]-4-methyl-1,3-thiazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

Dimethylamine (100 ml, 40% solution) was added to a solution of 5-(4-fluorobenzoyl)-4-methyl-2(3H)-thiazolone (4.7 g) in ethanol (200 ml). The mixture was stirred in a sealed stainless steel vessel at 120° C. for 16 hours. After cooling to ambient temperature the solvent and excess dimethylamino was evaporated. The residue was recrystallized twice from ethanol to give the title compound, mp. 224°-226° C.

Workup

  1. temperatureAfter cooling to ambient temperature the solvent and excess dimethylamino
  2. customwas evaporated
  3. customThe residue was recrystallized twice from ethanol

Sources & evidence

ORD record
ord-5cdcc43a60684ad0a8f5b3bcc3803dd8
Source dataset
uspto-grants-1988_03
Patent number
US04734422

Reaction notes

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