Acetyl chloride → HCID 9819853, compound

HRID 1062627Notes

Reaction equation

HRID 1062627 reaction equation
[CH3:1][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH2:22])[S:14][C:15]=2[C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)=[CH:7][CH:6]=1)([CH3:4])[CH3:3].[C:23](Cl)(=[O:25])[CH3:24].C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:4][C:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[C:13]([NH:22][C:23](=[O:25])[CH3:24])[S:14][C:15]=2[C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)=[CH:7][CH:6]=1)([CH3:1])[CH3:3]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 11335869HCID 11335869, compound

Product 1

HCID 9819853HCID 9819853, compoundYield 50.7%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of [4-[4-(1,1-dimethylethyl)phenyl]-5-(4-pyridyl)-1,3-thiazol-2-yl]amine (0.40 g, 1.29 mmol) and 4-dimethylaminopyridine (0.05 g, 0.39 mmol) in N,N-dimethylacetamide (4 mL) was added acetyl chloride (0.15 g, 1.94 mmol) and the mixture was stirred at 80° C. for 14 h. To the reaction mixture was poured aqueous sodium hydrogencarbonate and the precipitated solid was collected by filtration. The obtained solid was washed with water and dried. Crude crystals were recrystallized from ethanol to give the title compound (0.23 g, yield 50%).

Workup

  1. filtrationthe precipitated solid was collected by filtration
  2. washThe obtained solid was washed with water
  3. customdried
  4. customCrude crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-30a678e61c1444b4947dd3858e6e67e5
Source dataset
uspto-grants-2005_11
Patent number
US06962933B1

Reaction notes

Loading…