Methyl Isocyanate → HCID 5488733, compound

HRID 1074907Notes

Reaction equation

HRID 1074907 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[F:5][C:6]([F:13])([F:12])/[C:7](=[N:10]/[OH:11])/[S:8][CH3:9]>>[F:5][C:6]([F:13])([F:12])/[C:7](=[N:10]/[O:11][C:3](=[O:4])[NH:2][CH3:1])/[S:8][CH3:9]

Participants

3

Reactant 2

HCID 12228Methyl IsocyanateHCID 13003316HCID 13003316, compound

Product 1

HCID 5488733HCID 5488733, compoundYield 96%

Procedure

A mixture of 17.12 g (0.3 mol) of methyl isocyanate and 47.74 g (0.3 mol) of S-methyl (Z)-2,2,2-trifluoro-N-(hydroxy)thioacetimidate was sealed in a glass tube and heated at 100° in a steam bath for 17 hours. The contents of the tube were distilled at reduced pressure to give 62.02 g (96%) of S-methyl (Z)-2,2,2-trifluoro-N-(methylcarbamoyloxy)thioacetimidate as a colorless, viscous liquid: bp 96° (0.6 mm); nD25 1.4638; ir (neat) 5.73μ (C=O); 19F NMR (CFCl3) δ -64.6 ppm (q, J=1.2 Hz); 1H NMR (CFCl3) δ 2.63 ppm (q, J=1.2 Hz, 3H), 2.88 ppm (d, J=4.5 Hz, 3H) and 6.47 ppm (NH).

Workup

  1. customwas sealed in a glass tube
  2. temperatureheated at 100° in a steam bath for 17 hours
  3. distillationThe contents of the tube were distilled at reduced pressure

Sources & evidence

ORD record
ord-733e12ce40494d81be3d579660ab0647
Source dataset
uspto-grants-1983_07
Patent number
US04394386

Reaction notes

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