Hydrochloric Acid → 4-Amino-2-isopropyl-5-phenylazopyrimid-6-one

HRID 1288283Notes

Reaction equation

HRID 1288283 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.Cl.[NH2:18][C:19]1[N:20]=[C:21]([CH:26]([CH3:28])[CH3:27])[NH:22][C:23](=[O:25])[CH:24]=1.[OH-].[Na+]>O>[NH2:18][C:19]1[N:20]=[C:21]([CH:26]([CH3:28])[CH3:27])[NH:22][C:23](=[O:25])[C:24]=1[N:9]=[N:8][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6115AnilineHCID 14798Sodium HydroxideHCID 60992Benzenediazonium chlorideHCID 1355966346-Amino-2-isopropylpyrimidin-4-ol

Product 1

HCID 1363546184-Amino-2-isopropyl-5-phenylazopyrimid-6-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A cold solution of benzenediazonium chloride [prepared, by the method well known in the art, from 13.3 g. aniline in a 1:1 v/v mixture of water and concentrated hydrochloric acid (120 ml)] was added dropwise with stirring to a solution of 4-amino-2-isopropylpyrimid-6-one (28 g.) and sodium hydroxide (14.8 g.) in water (450 ml.) at 5° C. After stirring for a further 1 hour, the mixture was filtered. The filtrate was adjusted to pH 6 by the addition of aqueous sodium hydroxide solution, and the resultant solid was isolated to give crude 4-amino-2-isopropyl-5-phenylazopyrimid-6-one (33.5 g.), m.p. 215°-219° C. Recrystallisation from ethanol gave pure 4-amino-2-isopropyl-5-phenylazopyrimid-6-one (8.3 g.), m.p. 235°-236° C. (with decomposition).

Workup

  1. additionwas added dropwise
  2. filtrationthe mixture was filtered
  3. additionThe filtrate was adjusted to pH 6 by the addition of aqueous sodium hydroxide solution
  4. customthe resultant solid was isolated
  5. customto give crude 4-amino-2-isopropyl-5-phenylazopyrimid-6-one (33.5 g.), m.p. 215°-219° C
  6. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-0667211760c64cb194dea23c8a8fe957
Source dataset
uspto-grants-1976_10
Patent number
US03987160

Reaction notes

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