Hydrochloric Acid → 2,4-Diamino-6-methyl-5-(m-chlorophenylazo) pyrimidine

HRID 2082944Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[Cl:10][C:11]1[CH:12]=[C:13]([CH:15]=[CH:16][CH:17]=1)[NH2:14].Cl.[N:19]([O-])=O.[Na+].NC(N)=O.N1C=CC=NC=1.[OH-].[Na+]>O.C(O)C>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([N:19]=[N:14][C:13]2[CH:15]=[CH:16][CH:17]=[C:11]([Cl:10])[CH:12]=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. m-Chloro aniline (1.02 gm) was dissolved in ethanol (10 ml). To this solution 3 N HCl (30 ml) was added and the solution was cooled to -5° C. A solution of sodium nitrite (0.552 gm) in water (5 ml) was also cooled to 0° C. The cold sodium nitrite solution was then added to the cold m-chloro aniline solution. After shaking thoroughly, excess sodium nitrite was decomposed with a trace of urea. The diazotized m-chloro aniline solution 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 solution. A precipitate appeared. After stirring for two hours more, the product was separated by filtration, washed well with water, dried in a vacuum desiccator, and crystallized from ethanol. M.P. 249° C. Yield: 1.65 grams (85 percent).

Workup

stirringAfter shaking thoroughly
stirringAfter stirring for 10 minutes
stirringAfter stirring for two hours more
customthe product was separated by filtration
washwashed well with water
customdried in a vacuum desiccator
customcrystallized from ethanol

Sources & evidence

ORD record: ord-4de973a8f71f40f19b0c1d5c41bf1cd6
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04083841

Reaction notes

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