Aniline → HCID 136354621, compound

HRID 1288288Notes

Reaction equation

HRID 1288288 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH3:12])[NH:5][C:6](=[O:8])[CH:7]=1.[OH-].[Na+].[Cl-].[C:16]1([N+:22]#[N:23])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.NC1C=CC=CC=1>O>[NH2:1][C:2]1[N:3]=[C:4]([CH2:9][CH2:10][CH2:11][CH3:12])[NH:5][C:6](=[O:8])[C:7]=1[N:23]=[N:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6115AnilineHCID 14798Sodium Hydroxide2×HCID 60992Benzenediazonium chlorideHCID 136279932HCID 136279932, compound

Product 1

HCID 136354621HCID 136354621, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4-amino-2-butylpyrimid-6-one (7.65 g.) and sodium hydroxide (3.7 g.) in water (115 ml.) was added, at below 5° C, benzene diazonium chloride solution prepared (by the method well known in the art) from aniline (4.64 ml.), and the mixture was then heated to reflux for 1 hour. The pH was adjusted to 6 by the addition of aqueous sodium hydroxide solution, the product was filtered off, washed with water, dried and recrystallised from ethanol to give 4-amino-2-n-butyl-5-phenylazopyrimid-6-one (2.52 g.), m.p. 266°-270° C, pure enough for use in the next stage of the preparation.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureto reflux for 1 hour
  3. filtrationthe product was filtered off
  4. washwashed with water
  5. customdried
  6. customrecrystallised from ethanol

Sources & evidence

ORD record
ord-120d6d5b01ad465ea27f4359a4879bee
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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