Dimethylformamide → Methyl 4-[4-(4-chlorophenyl)-2-oxazolyl]benzoate

HRID 1264917Notes

Reaction equation

HRID 1264917 reaction equation
[C:1]([C:4]1[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[NH2:2].[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([C:19](=O)[CH2:20]Br)=[CH:17][CH:16]=1.CN(C)C=O>C(O)C>[Cl:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]2[N:2]=[C:1]([C:4]3[CH:13]=[CH:12][C:7]([C:8]([O:10][CH3:11])=[O:9])=[CH:6][CH:5]=3)[O:3][CH:20]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 68303p-Chlorophenacyl bromideHCID 596094Methyl 4-carbamoylbenzoate

Product 1

HCID 18613897Methyl 4-[4-(4-chlorophenyl)-2-oxazolyl]benzoateYield 18%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of methyl 4-carbamoylbenzoate (4.67 g), 4-chlorophenacyl bromide (6.50 g) and N,N-dimethylformamide (5 ml) was stirred at 130° C. for 2 hours. Hot ethanol was added to the reaction mixture, which was filtered. The filtrate was cooled to obtain crystals of methyl 4-[4-(4-chlorophenyl)-2-oxazolyl]benzoate (1.45 g, Yield: 18%). The product was recrystallized from ethanol. Pale yellow prisms. Melting Point: 183 to 184° C.

Workup

  1. filtrationwas filtered
  2. temperatureThe filtrate was cooled

Sources & evidence

ORD record
ord-9dd429ce3653460d904c96038eab3e6f
Source dataset
uspto-grants-2003_04
Patent number
US06545009B1

Reaction notes

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