Methyl Isocyanate → HCID 21539426, compound

HRID 1076196Notes

Reaction equation

HRID 1076196 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:9]([CH2:11][CH3:12])[CH3:10])[C:6]=1[C:7]#[N:8].[CH3:13][N:14]=[C:15]=[O:16]>C(COC)OC>[C:7]([C:6]1[C:5]([CH:9]([CH2:11][CH3:12])[CH3:10])=[CH:4][S:3][C:2]=1[NH:1][C:15]([NH:14][CH3:13])=[O:16])#[N:8]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 21539408HCID 21539408, compound

Product 1

HCID 21539426HCID 21539426, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 5 g 2-amino-3-cyano-4-sec-butylthiophene and 10 ml methyl isocyanate in 20 ml dimethoxyethane was stirred at about 25°C. for 2 days and then at reflux for 6 hours. The reaction mixture was evaporated under reduced pressure and the residue was chromatographed on a silica-gel column. The product, a white solid melting at 149°-152°C., was eluted with 70% ether-30% hexane. The infrared spectrum of the product showed cyano absorption at 4.5 microns. Sulfur analysis for the product is tabulated in Table I.

Workup

  1. temperatureat reflux for 6 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. customthe residue was chromatographed on a silica-gel column
  4. washThe product, a white solid melting at 149°-152°C., was eluted with 70% ether-30% hexane
  5. customcyano absorption at 4.5 microns

Sources & evidence

ORD record
ord-1b3a9ada0fa64eaf964cbd3dc0ec09d8
Source dataset
uspto-grants-1976_05
Patent number
US03956315

Reaction notes

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