Triethylamine → N-(5-isopropyl-1,3-thiazol-2-yl)-butanamide

HRID 1822877Notes

Reaction equation

HRID 1822877 reaction equation
C(N(CC)CC)C.[C:8](Cl)(=[O:12])[CH2:9][CH2:10][CH3:11].[NH2:14][C:15]1[S:16][C:17]([CH:20]([CH3:22])[CH3:21])=[CH:18][N:19]=1>ClCCl>[CH:20]([C:17]1[S:16][C:15]([NH:14][C:8](=[O:12])[CH2:9][CH2:10][CH3:11])=[N:19][CH:18]=1)([CH3:22])[CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8855Butyryl chlorideHCID 104869545-(Propan-2-yl)-1,3-thiazol-2-amine

Product 1

HCID 22170554N-(5-isopropyl-1,3-thiazol-2-yl)-butanamideYield 50.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-5 °C

Procedure

Triethylamine (0.97 ml; 6.34 mmol) and butanoyl chloride (0.52 ml; 5.07 mmol) were added in this order to a solution of 2-amino-5-isopropyl-1,3-thiazole (0.6 g; 4.23 mmol) in dichloromethane (8 ml), cooled to −5° C. The reaction mixture was stirred at −5° C. for 2 hours and then warmed to room temperature. After additional 4 hours, the organic layer was washed with water, saturated sodium bicarbonate, 1N hydrochloric acid, brine, dried over sodium sulfate and evaporated. The residue was recrystallized from cyclohexane to yield 0.45 g (50%) of the title compound as a colourless solid (m.p. 95–97° C.)

Workup

  1. temperaturewarmed to room temperature
  2. waitAfter additional 4 hours
  3. washthe organic layer was washed with water, saturated sodium bicarbonate, 1N hydrochloric acid, brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was recrystallized from cyclohexane

Sources & evidence

ORD record
ord-147b18c32f1741f389eb071fac135d61
Source dataset
uspto-grants-2006_05
Patent number
US07037929B1

Reaction notes

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