Water → HCID 12851817, compound

HRID 1156890Notes

Reaction equation

HRID 1156890 reaction equation
[C-:1]#[N:2].[Na+].[N+:4]([C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22]Cl)=[O:12])=[CH:9][CH:8]=1)([O-:6])=[O:5].O>CS(C)=O>[N+:4]([C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH2:22][C:1]#[N:2])=[O:12])=[CH:9][CH:8]=1)([O-:6])=[O:5]

Participants

5

Reactant 3

HCID 962WaterHCID 8929Sodium CyanideHCID 12851816HCID 12851816, compound

Product 1

HCID 12851817HCID 12851817, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Sodium cyanide (2.9 g) was dissolved in 100 ml of dimethylsulfoxide, and with stirring at room temperature, 15.5 g of 1-(4-nitrobenzoyl)amino-2-(2-chloromethylphenyl)ethane was gradually added. The reaction was performed at room temperature for 10 hours. The reaction mixture was poured into water, extracted with ethyl acetate, washed in water, and dried. The solvent was distilled off, and the residue was recrystallized from ethanol to afford 11.2 g of 1-(4-nitrobenzoyl)amino-2-(2-cyanomethylphenyl)ethane having a melting point of 118.6° to 119.1° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed in water
  3. customdried
  4. distillationThe solvent was distilled off
  5. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-bac7a7d507194f36a88e39041c1eb052
Source dataset
uspto-grants-1982_06
Patent number
US04337256

Reaction notes

Loading…