4-Nitrobenzamide → HCID 57465380, compound

HRID 1951594Notes

Reaction equation

HRID 1951594 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[Cl:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17](=O)[CH2:18]Br>CN1C(=O)CCC1.C1(C)C=CC=CC=1>[Cl:13][C:14]1[CH:15]=[C:16]([C:17]2[N:10]=[C:8]([C:7]3[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[O:9][CH:18]=2)[CH:21]=[CH:22][CH:23]=1

Participants

5

Reactant 2

HCID 120914-NitrobenzamideHCID 387382-Bromo-3'-chloroacetophenone

Product 1

HCID 57465380HCID 57465380, compoundYield 43.4%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
135 °C

Procedure

under an N2 atmosphere, 4-nitrobenzamide (5.3 g, 32 mmol) and 3-chlorophenacyl bromide (4.9 g, 21 mmol) were combined in NMP (3.0 mL) and heated to 135° C. After 2.5 hours at 135° C., the reaction was diluted with 20 mL of toluene and allowed to cool to room temperature. The solid was removed by filtration and the filtrate was concentrated in vacuo. The resulting solid from concentration of the filtrate was triturated with ethyl acetate. The solid was collected by filtration and afforded 4-(3-chlorophenyl)-2-(4-nitrophenyl)oxazole (2.74 g, 43% yield). ESI m/z=301.0 (M+H+).

Workup

  1. temperatureto cool to room temperature
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe resulting solid from concentration of the filtrate was triturated with ethyl acetate
  5. filtrationThe solid was collected by filtration

Sources & evidence

ORD record
ord-c6b6d897ac3f43cbada7df6f9f66c9ff
Source dataset
uspto-grants-2013_03
Patent number
US08404722B2

Reaction notes

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