Urea → HCID 54327178, compound

HRID 2082946Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[I: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]([I: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-Iodo aniline (1.84 gm) was dissolved in ethanol (30 ml) and to this solution 3 N HCl (30 ml) was added. The solution was then cooled to -5° C. A solution of sodium nitrite (0.567 gm) in water (5 ml) was also cooled to 0° C. The sodium nitrite solution was then added to the p-iodo aniline solution. After shaking thoroughly, excess sodium nitrite was decomposed with a pinch of urea. The diazotized p-iodo aniline was then added to the pyrimidine solution. After stirring for ten minutes, the pH of the combined solution was adjusted to 7.0 with 30 percent sodium hydroxide. A precipitate appeared. After stirring two hours more, the product was filtered, dried in vacuum desiccator, and crystallized from ethanol. M.P. 243°-44° C. Yield: 2.5 gm (90 percent).

Workup

additionwas added
stirringAfter shaking thoroughly
stirringAfter stirring for ten minutes
stirringAfter stirring two hours more
filtrationthe product was filtered
customdried in vacuum desiccator
customcrystallized from ethanol

Sources & evidence

ORD record: ord-82d5eefb318140829abf34ca1aeb4ded
Source dataset: uspto-grants-1978_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04083841

Reaction notes

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