Methyl 4-(chlorocarbonyl)benzoate → HCID 18446666, compound

HRID 1268748Notes

Reaction equation

HRID 1268748 reaction equation
Cl[C:2]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)=[O:3].[CH3:14][C:15]1[CH:16]=[C:17]([C:21]2[N:22]=[C:23]([NH2:32])[S:24][C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][N:27]=2)[CH:18]=[CH:19][CH:20]=1.C(=O)([O-])O.[Na+]>CN(C)C1C=CN=CC=1.CN(C)C(=O)C>[CH3:14][C:15]1[CH:16]=[C:17]([C:21]2[N:22]=[C:23]([NH:32][C:2]([C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)=[O:3])[S:24][C:25]=2[C:26]2[CH:31]=[CH:30][N:29]=[CH:28][N:27]=2)[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 81850Methyl 4-(chlorocarbonyl)benzoateHCID 516892Sodium BicarbonateHCID 17863040HCID 17863040, compound

Product 1

HCID 18446666HCID 18446666, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 31374DimethylacetamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 4-chloroformylbenzoate (1.1 g, 5.6 mmol) was added to a solution of [4-(3-methylphenyl)-5-(4-pyrimidinyl)-1,3-thiazol-2-yl]amine and 4-dimethylaminopyridine (0.14 g, 1.1 mmol) in N,N-dimethylacetamide (10 mL), and the mixture was stirred at 70° C. for 14 hrs. Aqueous sodium hydrogen carbonate solution was added to the reaction mixture and the precipitated solids were collected by filtration. Crude crystals were washed with water, dried and recrystallized from pyridine to give the title compound (1.0 g, yield 65%).

Workup

  1. filtrationthe precipitated solids were collected by filtration
  2. washCrude crystals were washed with water
  3. customdried
  4. customrecrystallized from pyridine

Sources & evidence

ORD record
ord-e9dfb1b2bbae4850b5b4e10713bcb0f7
Source dataset
uspto-grants-2007_04
Patent number
US07199124B2

Reaction notes

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