Ethanol → HCID 10308522, compound

HRID 729343Notes

Reaction equation

HRID 729343 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[NH:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[N+]([O-])(O)=O.[NH2:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=1)[C:21]#[N:22].[N:26]#CN.[CH3:29][CH2:30]O>O.CCOCC>[N:22]1[N:26]2[N:17]=[CH:18][CH:25]=[CH:24][C:23]2=[C:20]([C:19]2[CH:30]=[CH:29][N:12]=[C:10]([NH:9][C:5]3[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=3)[C:1]#[N:2])[N:11]=2)[CH:21]=1

Participants

8

Reactant 5

HCID 702EthanolHCID 944Nitric Acid2×HCID 9864CyanamideHCID 167023-AminobenzonitrileHCID 178509849HCID 178509849, compound

Product 1

HCID 10308522HCID 10308522, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
100 °C

Procedure

N-(3-Cyanophenyl)guanidine.HNO3. To a solution of 3-aminobenzonitrile (3.31 g, 28 mmol) in EtOH (28 mL) was added cyanamide (2.5 mL of a 50% w/w solution in water). HNO3 (1.98 mL, 14.2 M) is added dropwise. The mixture was heated at an oil bath temperature of 100° C. for about 3 hours. The flask was allowed to cool to RT. Et2O (20 mL) was added and the solids isolated by filtration. The solids were dried under vacuum (1 torr) for about 18 hours to give the title compound as a beige powder (2.9 g, 46%). 1H-NMR (300 MHz, d6-DMSO) δ 9.80 (s, 1H), 7.77 (m, 2H), 7.69-7.57 (m, 6H); MS (ESI) (M+H)+ 161.

Workup

  1. temperatureto cool to RT
  2. customthe solids isolated by filtration
  3. customThe solids were dried under vacuum (1 torr) for about 18 hours

Sources & evidence

ORD record
ord-b8ae895f9ca44d72a2ae8bbd5b1c3c2d
Source dataset
uspto-grants-2009_09
Patent number
US07582630B2

Reaction notes

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