Aniline → 4-Amino-2-benzyl-5-phenylazopyrimid-6-one

HRID 1288280Notes

Reaction equation

HRID 1288280 reaction equation
[Cl-].[C:2]1([N+:8]#[N:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.NC1C=CC=CC=1.[NH2:17][C:18]1[N:19]=[C:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:21][C:22](=[O:24])[CH:23]=1.[OH-].[Na+]>O>[NH2:17][C:18]1[N:19]=[C:20]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[NH:21][C:22](=[O:24])[C:23]=1[N:9]=[N:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium HydroxideHCID 60992Benzenediazonium chlorideHCID 1355966376-amino-2-benzylpyrimidin-4(3H)-one

Product 1

HCID 1363546174-Amino-2-benzyl-5-phenylazopyrimid-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A cold solution of benzenediazonium chloride (prepared by the method well known in the art, from 2 g. aniline) was added dropwise with stirring to a solution of 4-amino-2-benzylpyrimid-6-one (4 g.) and sodium hydroxide (1.6 g.) in water (50 ml.) at 5° C. After stirring for a further 1 hour, the solid was filtered off and recrystallised from a mixture of dimethylformamide and water (4:1 v/v) to give 4-amino-2-benzyl-5-phenylazopyrimid-6-one (3.8 g.) in the form of orange needles, which decomposed at 256°-257° C.

Workup

  1. filtrationthe solid was filtered off
  2. customrecrystallised from a mixture of dimethylformamide and water (4:1 v/v)

Sources & evidence

ORD record
ord-1229000a61ef4024aaa189480fc98870
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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