Urea → 2,4-Diamino-6-methyl-5-(p-bromophenylazo) pyrimidine

HRID 2082945Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Br:10][C:11]1[CH:17]=[CH:16][C:14]([NH2:15])=[CH:13][CH:12]=1.[N:18]([O-])=O.[Na+].NC(N)=O.N1C=CC=NC=1.[OH-].[Na+]>O.C(O)C.Cl>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:18]=[N:15][C:14]2[CH:16]=[CH:17][C:11]([Br:10])=[CH:12][CH:13]=2)=[C:4]([CH3:9])[N:3]=1

Participants

Conditions

Temperature: -5 °C

Procedure

A solution of 2,4-diamino-6-methyl pyrimidine (1.0 gm) in water (60 ml) was cooled to 0° C in ice-salt bath and stirred mechanically. p-Bromo aniline (1.38 gm) was dissolved in ethanol (30 ml) and to this solution 3 N HCl (30 ml) was added. The solution was then allowed to cool to -5° C. A solution of sodium nitrite (0.553 gm) in water (5 ml) was cooled to 0° C. The sodium nitrite solution was then added to the p-bromo aniline solution. After shaking thoroughly, excess sodium nitrite was decomposed with a pinch of urea. The diazotized p-bromo aniline was then added to the pyrimidine solution. After stirring for 10 minutes, the pH of the combined solution was adjusted to 7.0 with 30 percent sodium hydroxide. A precipitate appeared. After stirring for 2 hours more, the product was separated by filtration, dried in vacuum desiccator, and crystallized from butanol. M.P. 245°-46° C. Yield: 2.2 gm (90 percent).

Workup

additionwas added
stirringAfter shaking thoroughly
stirringAfter stirring for 10 minutes
stirringAfter stirring for 2 hours more
customthe product was separated by filtration
customdried in vacuum desiccator
customcrystallized from butanol

Sources & evidence

ORD record: ord-811f3de4fd26447a8736357753b736ff
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04083841

Reaction notes

Loading…