Cyanamide → N-Cyano-N'-[4-(1H-imidazol-2-yl)phenyl]methanimidamide

HRID 979194Notes

Reaction equation

HRID 979194 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][CH:3]=1.[N:13]#[C:14][NH2:15].[CH:16](OCC)(OCC)OCC>>[C:14]([NH:15][CH:16]=[N:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[NH:12][CH:11]=[CH:10][N:9]=2)=[CH:6][CH:7]=1)#[N:13]

Participants

4

Reactant 3

HCID 9864CyanamideHCID 31214Ethyl orthoformateHCID 235069274-(1H-Imidazol-2-yl)aniline

Product 1

HCID 20201830N-Cyano-N'-[4-(1H-imidazol-2-yl)phenyl]methanimidamideYield 62.2%

Conditions

Temperature
150 °C

Procedure

A mixture of 2-(4-amino-phenyl)-1-H-imidazole (3.1 g), cyanamide (0.8 g) and triethyl orthoformate (3.6 g) was heated at 150° C. for a few minutes. The product which crystallized out was filtered off, washed with ethanol and dried to give 2.5 g of the title compound, M.p. 228°-229° C.

Workup

  1. customThe product which crystallized out
  2. filtrationwas filtered off
  3. washwashed with ethanol
  4. customdried

Sources & evidence

ORD record
ord-6b37d5cd0c2a45cbbd51768450d45946
Source dataset
uspto-grants-1987_05
Patent number
US04666932

Reaction notes

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