Nitric Acid → HCID 178426711, compound

HRID 440870Notes

Reaction equation

HRID 440870 reaction equation
[N+:1]([O-:4])([OH:3])=[O:2].[NH2:5][C:6]1[CH:11]=[C:10]([N+:12]([O-:14])=[O:13])[CH:9]=[CH:8][C:7]=1[CH3:15].[N:16]#[C:17][NH2:18]>C(O)C.O>[N+:1]([O-:4])([OH:3])=[O:2].[CH3:15][C:7]1[CH:8]=[CH:9][C:10]([N+:12]([O-:14])=[O:13])=[CH:11][C:6]=1[NH:5][C:17]([NH2:18])=[NH:16]

Participants

6

Reactant 3

HCID 944Nitric AcidHCID 74442-Methyl-5-NitroanilineHCID 9864Cyanamide

Product 1

HCID 178426711HCID 178426711, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

9.1 ml (0.13 mol) of 65% nitric acid are added dropwise in the course of 5 minutes to a yellow suspension of 20.0 g (0.13 mol) of 2-amino-4-nitrotoluene in 50 ml of absolute ethanol. When the exothermic reaction has subsided, 8.32 g (0.198 mol) of cyanamide dissolved in 8.3 ml of water are added. The brown reaction mixture is boiled at reflux for 25 hours, cooled to 0° and filtered. Washing with 4×100 mi of ethanol/diethyl ether (1:1) and drying yield 2-methyl-5-nitrophenyl-guanidine nitrate; m.p. 219°-226°.

Workup

  1. customWhen the exothermic reaction
  2. additionare added
  3. temperatureat reflux for 25 hours
  4. temperaturecooled to 0°
  5. filtrationfiltered
  6. washWashing with 4×100 mi of ethanol/diethyl ether (1:1)
  7. customdrying

Sources & evidence

ORD record
ord-bb58e7b4331e41ee8af8bf942ada1173
Source dataset
uspto-grants-1996_05
Patent number
US05521184

Reaction notes

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