2-(Bis(methylsulfanyl)methylidene)propanedinitrile → HCID 21190620, compound

HRID 1068947Notes

Reaction equation

HRID 1068947 reaction equation
CS[C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6].[C:11]([NH:18][CH2:19][C:20]1[CH:21]=[C:22]([CH:24]=[CH:25][CH:26]=1)[NH2:23])([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]>CO>[C:11]([NH:18][CH2:19][C:20]1[CH:21]=[C:22]([NH:23][C:3]([S:9][CH3:10])=[C:4]([C:7]#[N:8])[C:5]#[N:6])[CH:24]=[CH:25][CH:26]=1)([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12]

Participants

4

Reactant 2

HCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrileHCID 10775412tert-butyl N-((3-aminophenyl)methyl)carbamate

Product 1

HCID 21190620HCID 21190620, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 102.1 g (600 mmol) of 3,3-bis-methylmercapto-2-cyano-acrylonitrile, 133.3 g (600 mmol) of 3-(N-Boc-aminomethyl)-aniline (WO 93/00095) and 1100 ml of methanol is heated under reflux for 6.5 hours and then concentrated by evaporation in vacuo. Crystallization of the residue from ethyl acetate, filtration and washing the filtration residue with ethyl acetate yield 3-[3-(N-Boc-aminomethyl)-phenylamino]-2-cyano-3-methylmercapto-acrylonitrile; m.p. 150-151° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6.5 hours
  3. concentrationconcentrated by evaporation in vacuo
  4. customCrystallization of the residue
  5. filtrationfrom ethyl acetate, filtration
  6. washwashing the filtration residue with ethyl acetate

Sources & evidence

ORD record
ord-6a22e000ac154f68b82b42ad47010123
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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