2-(Bis(methylsulfanyl)methylidene)propanedinitrile → HCID 19610562, compound

HRID 1602298Notes

Reaction equation

HRID 1602298 reaction equation
CS[C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6].[C:11]([NH:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>CO>[C:11]([NH:18][C:19]1[CH:20]=[CH:21][C:22]([NH:25][C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])=[CH:23][CH:24]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 688611tert-Butyl (4-aminophenyl)carbamate

Product 1

HCID 19610562HCID 19610562, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 13.89 g (81.58 mmol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile, 17 g (81.63 mmol) of N-BOC-1,4-phenylenediamine (Fluka) and 200 ml of methanol is heated under reflux for 5 hours. Cooling to room temperature, filtering and washing the filter residue with methanol yield the title compound; m.p. 190° C. Concentration of the filtrate by evaporation and recrystallization of the residue from 50 ml of methanol yield a further batch of the title compound; m.p. 190-191° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. filtrationfiltering
  4. washwashing the filter residue with methanol

Sources & evidence

ORD record
ord-2ce3518ec1d0414289c9962b6428274e
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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