Methyl Isocyanate → N-Methyl-N(4-t-Butylphenylthiosulfenyl) Carbamoyl Fluoride

HRID 372369Notes

Reaction equation

HRID 372369 reaction equation
[FH:1].[CH3:2][N:3]=[C:4]=[O:5].[C:6]([C:10]1[CH:15]=[CH:14][C:13]([S:16][S:17]Cl)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7]>C1(C)C=CC=CC=1>[CH3:2][N:3]([S:17][S:16][C:13]1[CH:14]=[CH:15][C:10]([C:6]([CH3:9])([CH3:8])[CH3:7])=[CH:11][CH:12]=1)[C:4]([F:1])=[O:5]

Participants

5

Reactant 3

HCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 205604854-t-Butylphenylthiosulfenyl chloride

Product 1

HCID 23333006N-Methyl-N(4-t-Butylphenylthiosulfenyl) Carbamoyl Fluoride

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5.5 g hydrogen fluoride in toluene cooled to -65° C was added dropwise with stirring 15.0 ml of methylisocyanate over a period of 20 minutes after stirring for 1.5 hr preshly prepared 4-t-butylphenylthiosulfenyl chloride (prepared from 36.2 g 4-t-butylthiophenol and 31.0 g sulfur dichloride in 800 ml ethyl ether) was added at -10° to 0° C over a period of 0.5 hr. After stirring overnight at ambient temperature, the salt was removed by filtration and the filtrate distilled. b.p. 122°-127° C/0.2 Torr.

Workup

  1. additionwas added dropwise
  2. additionwas added at -10° to 0° C over a period of 0.5 hr
  3. customthe salt was removed by filtration
  4. distillationthe filtrate distilled

Sources & evidence

ORD record
ord-fa79a2480cca4405844e816195f5ce99
Source dataset
uspto-grants-1978_05
Patent number
US04091016

Reaction notes

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