2-ethylhexanoic acid tin(II) salt → HCID 23452261, compound

HRID 1277862Notes

Reaction equation

HRID 1277862 reaction equation
O[CH:2]([C:4](=[CH2:7])[C:5]#[N:6])[CH3:3].CCCCC(C([O-])=O)CC.CCCCC(C([O-])=O)CC.[Sn+2].[CH3:29][N:30]=[C:31]=[O:32].[N-]=C=O>>[C:5]([C:4]([CH:2]([C:31](=[O:32])[NH:30][CH3:29])[CH3:3])=[CH2:7])#[N:6]

Participants

5

Reactant 4

HCID 93182-ethylhexanoic acid tin(II) saltHCID 12228Methyl IsocyanateHCID 105034IsocyanateHCID 109754123-Hydroxy-2-methylidenebutanenitrile

Product 1

HCID 23452261HCID 23452261, compound

Procedure

2-Cyano-3-(N-methyl carbamyl)-1-butene was prepared through the following reaction. A three-necked 250 ml round bottom flask equipped with an overhead stirrer, N2 inlet, water condenser and dropping funnel was charged with 47.5 parts 2-(1-hydroxyethyl) acrylonitrile and 0.71 parts stannous octoate. To this stirred mixture, 28.5 parts methyl isocyanate was added through the dropping funnel. The mixture was maintained below 35° C. during addition by cooling and adjustment of the addition rate of the isocyanate. After the addition was complete, the mixture was stirred for an additional six hours. The product was then subjected to reduced pressure to remove any unreacted methyl isocyanate. The product was obtained as a viscous oil.

Workup

  1. customA three-necked 250 ml round bottom flask equipped with an overhead stirrer, N2 inlet, water condenser
  2. temperatureThe mixture was maintained below 35° C. during addition
  3. temperatureby cooling
  4. additionAfter the addition
  5. customto remove any unreacted methyl isocyanate
  6. customThe product was obtained as a viscous oil

Sources & evidence

ORD record
ord-245000bf7e7d4c45846dc1027a448d77
Source dataset
uspto-grants-1981_07
Patent number
US04279833

Reaction notes

Loading…