Benzoyl chloride → N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

HRID 637486Notes

Reaction equation

HRID 637486 reaction equation
Br.[NH2:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:5][CH:4]=1.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>[OH-].[Na+]>[C:16]([NH:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[N:10]=[CH:11][C:12](=[O:15])[NH:13][CH:14]=2)=[CH:7][CH:8]=1)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 202086625-(4-Aminophenyl)-2(1H)-pyrazinone hydrobromide

Product 1

HCID 20208664N-[4-(5-Oxo-4,5-dihydropyrazin-2-yl)phenyl]benzamide

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-(4-aminophenyl)-2(1H)-pyrazinone hydrobromide (2.0 g) in aqueous sodium hydroxide (46 ml, 10%) was treated with benzoyl chloride (1.9 ml) and the mixture was agitated for 2 hours at room temperature. The pale yellow precipitate was collected, washed with water and dried. Recrystallisation from glacial acetic acid gave the title compound (0.9 g), m.p.>300° C.; ν(Nujol mull) 1660 (C=0), 1705 (C=0), 3330 (NH)cm-1.

Workup

  1. customThe pale yellow precipitate was collected
  2. washwashed with water
  3. customdried
  4. customRecrystallisation from glacial acetic acid

Sources & evidence

ORD record
ord-b23ce0e9ef2c48649d34d0e8c70571af
Source dataset
uspto-grants-1985_12
Patent number
US04556711

Reaction notes

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