Methyl isothiocyanate → 1-Methyl-3-trifluoromethanesulphonylthiourea

HRID 364275Notes

Reaction equation

HRID 364275 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[F:5][C:6]([F:12])([F:11])[S:7]([NH2:10])(=[O:9])=[O:8].[OH-].[Na+]>CC(C)=O.O>[CH3:1][NH:2][C:3]([NH:10][S:7]([C:6]([F:12])([F:11])[F:5])(=[O:9])=[O:8])=[S:4]

Participants

6

Reactant 3

HCID 11167Methyl isothiocyanateHCID 14798Sodium HydroxideHCID 79001Trifluoromethylsulfonamide

Product 1

HCID 212988821-Methyl-3-trifluoromethanesulphonylthioureaYield 42.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of methylisothiocyanate (0.21 g.) in acetone (10 ml.) was added to a solution of trifluoromethanesulphonamide (0.45 g.) and sodium hydroxide (0.12 g.) in water (5 ml.), the mixture stirred at 60° for 18 hours and then evaporated to dryness. The residue was dissolved in water and the solution washed with ethyl acetate and then adjusted to pH 1 with concentrated hydrochloric acid. The mixture was treated with charcoal and filtered and the filtrate extracted with ethyl acetate. The combined ethyl acetate extracts were dried and evaporated to dryness and the residue recrystallised from petroleum ether (b.p. 60°-80°) to give 1-methyl-3-trifluoromethanesulphonylthiourea (0.27 g.), m.p. 88°-90°.

Workup

  1. customevaporated to dryness
  2. dissolutionThe residue was dissolved in water
  3. washthe solution washed with ethyl acetate
  4. additionThe mixture was treated with charcoal
  5. filtrationfiltered
  6. extractionthe filtrate extracted with ethyl acetate
  7. dry with materialThe combined ethyl acetate extracts were dried
  8. customevaporated to dryness
  9. customthe residue recrystallised from petroleum ether (b.p. 60°-80°)

Sources & evidence

ORD record
ord-9af2fa82a3d64c4b9413c5ffa41d9449
Source dataset
uspto-grants-1986_08
Patent number
US04604465

Reaction notes

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