Acetyl chloride → HCID 18446678, compound

HRID 1268750Notes

Reaction equation

HRID 1268750 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])[N: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])[N:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 516892Sodium BicarbonateHCID 17862961HCID 17862961, compound

Product 1

HCID 18446678HCID 18446678, compoundYield 61%

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-pyrimidinyl)-1,3-thiazol-2-yl]amine (0.50 g, 1.8 mmol) and 4-dimethylaminopyridine (0.065 g, 0.53 mmol) in N,N-dimethylacetamide (10 mL) was added acetylchloride (0.19 mL, 2.7 mmol), and the mixture was stirred at 80° C. for 14 hrs. Into the reaction mixture was poured aqueous sodium hydrogen carbonate solution and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated. The resulting crystals were recrystallized from ethyl acetate to give the title compound (0.35 g, yield 61%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. customdried
  4. concentrationconcentrated
  5. customThe resulting crystals were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b73237ca94864b5a80cb4dfb7cbf53d5
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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