Ethyl isocyanate → HCID 54067828, compound

HRID 839066Notes

Reaction equation

HRID 839066 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([OH:19])([C:15]([F:18])([F:17])[F:16])[C:11]([F:14])([F:13])[F:12])=[CH:5][C:4]=1[CH3:20].[CH2:21]([N:23]=[C:24]=[O:25])[CH3:22]>CCOCC>[CH2:21]([NH:23][C:24]([N:2]([CH3:1])[C:3]1[C:8]([CH3:9])=[CH:7][C:6]([C:10]([OH:19])([C:11]([F:12])([F:13])[F:14])[C:15]([F:16])([F:17])[F:18])=[CH:5][C:4]=1[CH3:20])=[O:25])[CH3:22]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 54026482HCID 54026482, compound

Product 1

HCID 54067828HCID 54067828, compoundYield 83.3%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Heat at reflux for three hours 13.5 g of N,2,6-trimethylaniline (0.100 mole) and 40 g of hexafluoroacetone sesquihydrate (0.21 mole). Allow to cool, pour onto water. Collect the solid, dry and recrystallize from ether-hexane to give 27.9 g white solid; m.p. 143°-144° C. Dissolve 6 g of the product, N,2,6-trimethyl-4-(hexafluoro-2-hydroxy-2-propyl)aniline (20 mmole) and 5.4 g of ethyl isocyanate (80 mmole) in Et2O. After 16 hours, concentrate and recrystallize the residual solid from etherhexane to give 6.2 g of a white solid; m.p. 178°-179° C.

Workup

  1. concentrationconcentrate
  2. customrecrystallize the residual solid from etherhexane

Sources & evidence

ORD record
ord-94c22c9df40a4500b34c9f7d3e8e989e
Source dataset
uspto-grants-1978_06
Patent number
US04093742

Reaction notes

Loading…