Nitric Acid → HCID 10308522, compound

HRID 1179126Notes

Reaction equation

HRID 1179126 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.CCO[CH2:32][CH3:33]>O>[N:22]1[N:26]2[N:17]=[CH:18][CH:25]=[CH:24][C:23]2=[C:20]([C:19]2[CH:33]=[CH:32][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

7

Reactant 5

HCID 944Nitric Acid2×HCID 3283Diethyl EtherHCID 9864CyanamideHCID 167023-AminobenzonitrileHCID 178509849HCID 178509849, compound

Product 1

HCID 10308522HCID 10308522, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

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-7beba1f0840f4a1d9918cc2d9f12fa03
Source dataset
uspto-grants-2007_10
Patent number
US07279473B2

Reaction notes

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