Methyl Isocyanate → HCID 21539419, compound

HRID 1076197Notes

Reaction equation

HRID 1076197 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH:9]2[CH2:11][CH2:10]2)[C:6]=1[C:7]#[N:8].[CH3:12][N:13]=[C:14]=[O:15].C([O-])(=O)CCCCCCCCCCC.C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC>C(COC)OC>[C:7]([C:6]1[C:5]([CH:9]2[CH2:10][CH2:11]2)=[CH:4][S:3][C:2]=1[NH:1][C:14]([NH:13][CH3:12])=[O:15])#[N:8]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 9809426Di-n-butyldilauryltinHCID 14142701HCID 14142701, compound

Product 1

HCID 21539419HCID 21539419, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 10 g 2-amino-3-cyano-4-cyclopropylthiophene, 6.94 g methyl isocyanate and 0.1 g dibutyl tin dilaurate in 20 ml dimethoxyethane was refluxed for 7 hours and then allowed to stand at about 25°C. overnight. The reaction mixture was evaporated and the resulting residue was chromatographed on silica gel. The product, a pale-green solid melting at 169°-172°C., was eluted with 1:1 ether-hexane. Sulfur analysis for the product is tabulated in Table I.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe resulting residue was chromatographed on silica gel
  3. washThe product, a pale-green solid melting at 169°-172°C., was eluted with 1:1 ether-hexane

Sources & evidence

ORD record
ord-cd603a8541974ff09d8da7e1df06f66e
Source dataset
uspto-grants-1976_05
Patent number
US03956315

Reaction notes

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