Acetyl chloride → N-[4-(3-METHYLPHENYL)-5-(2-METHYL-4-PYRIDYL)-1,3-THIAZOL-2-YL]ACETAMIDE

HRID 1727360Notes

Reaction equation

HRID 1727360 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH2:20])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[C:21](Cl)(=[O:23])[CH3:22].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([C:8]2[N:9]=[C:10]([NH:20][C:21](=[O:23])[CH3:22])[S:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[C:15]([CH3:19])[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 9965557HCID 9965557, compound

Product 1

HCID 9967012N-[4-(3-METHYLPHENYL)-5-(2-METHYL-4-PYRIDYL)-1,3-THIAZOL-2-YL]ACETAMIDEYield 67%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-(3-methylphenyl)-5-(2-methyl-4-pyridyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.8 mmol) and 4-dimethylaminopyridine (0.061 g, 0.50 mmol) in N,N-dimethylacetamide (15 mL) was added acetyl chloride (0.19 mL, 2.7 mmol), and the mixture was stirred for 14 hours at 80° C. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and the deposited solid was filtrated. The resulted solid was washed with water, then, dried. The crude crystal was recrystallized from ethanol, to obtain a title compound (0.39 g, yield 67%).

Workup

  1. filtrationthe deposited solid was filtrated
  2. washThe resulted solid was washed with water
  3. customdried
  4. customThe crude crystal was recrystallized from ethanol

Sources & evidence

ORD record
ord-7b6419a85d3d46c18b2f9f9a55496972
Source dataset
uspto-grants-2009_02
Patent number
US07495018B2

Reaction notes

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