Triethylamine → N-methyl-N-[4-(tert-butyl)phenylthio]carbamoyl fluoride

HRID 1834889Notes

Reaction equation

HRID 1834889 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]Cl)=[CH:12][CH:11]=1)([CH3:9])([CH3:8])[CH3:7].C(N(CC)CC)C>O.C1(C)C=CC=CC=1>[CH3:2][N:3]([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

8

Reactant 5

HCID 8471TriethylamineHCID 12228Methyl Isocyanate2×HCID 14917Hydrofluoric AcidHCID 12801136p-t-Butylbenzenesulfenyl chloride2×HCID 178435178HCID 178435178, compound

Product 1

HCID 12801137N-methyl-N-[4-(tert-butyl)phenylthio]carbamoyl fluorideYield 61%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
-10 °C

Procedure

To 1200 L ml of toluene at (-40°)-(20° C) in a one-gallon polypropylene bottle containing a stirrer, was added with stirring 37.4 grams (1.87 moles) of liquid hydrogen fluoride. The reaction mixture was raised to -10° C and 107 grams (1.87 moles) of methyl isocyanate was added with stirring and cooling. The reaction mixture was stirred for 1 hour at 0° C after the methyl isocyanate addition. To this mixture was then added 375 grams (1.87 moles) of 4-(tert-butyl) phenylsulfenyl chloride at 0° C over a 2 minute period. After the 4-(tert-butyl) phenylsulfenyl chloride addition, 189 grams (1.87 moles) of triethylamine was added slowly, with cooling and stirring. The reaction mixture was then warmed to 25° C and stirred overnight when it was added to 1000 ml of water. The toluene layer was washed four times with water and dried with magnesium sulfate after which it was distilled through a 1-foot packed column to give 275 grams of N-methyl-N-[4-(tert-butyl)phenylthio]carbamoyl fluoride, b.p. 122°/1.0 mm (yield 61%). The nmr spectrum agreed with the proposed structure.

Workup

  1. additionwas added
  2. temperaturecooling
  3. stirringThe reaction mixture was stirred for 1 hour at 0° C
  4. additionwas added slowly
  5. temperaturewith cooling
  6. stirringstirring
  7. temperatureThe reaction mixture was then warmed to 25° C
  8. stirringstirred overnight when it
  9. washThe toluene layer was washed four times with water
  10. dry with materialdried with magnesium sulfate after which it
  11. distillationwas distilled through a 1-foot

Sources & evidence

ORD record
ord-15e13f73041342b4ba6c21fe86304595
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

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