Dichloromethane → Diethylamino-sulfenyl carbamoyl fluoride

HRID 1834890Notes

Reaction equation

HRID 1834890 reaction equation
[FH:1].C(Cl)Cl.C[N:6]=[C:7]=[O:8].[CH2:9]([N:11]([CH2:14][CH3:15])[S:12]Cl)[CH3:10]>C(N(CC)CC)C>[CH2:9]([N:11]([CH2:14][CH3:15])[S:12][NH:6][C:7]([F:1])=[O:8])[CH3:10]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 12297776N,N-diethylaminosulfenyl chloride

Product 1

HCID 131711024Diethylamino-sulfenyl carbamoyl fluorideYield 62.9%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Anhydrous hydrogen fluoride (3.0 g, 0.15 mole) was added to 150 ml of methylene chloride at -10° C. Then 8.6 g of methylisocyanate was added, followed by 20.9 g (0.15 mole) of N,N-diethylaminosulfenyl chloride at 0° C. Triethylamine (15.2 g) was then added at 0° C over a 15-minute period, and the mixture was stirred at +5° C for 1 hour. The mixture was then extracted with water (100 ml), saturated sodium bicarbonate solution, and water again. After drying (MgSO4), the solvent was removed in vacuo, and the crude residue was vacuum distilled to give 17 g of N-methyl-N-(diethylamino-sulfenyl carbamoyl fluoride, b.p. 57° C/0.8 mm (62.9 percent yield).

Workup

  1. extractionThe mixture was then extracted with water (100 ml), saturated sodium bicarbonate solution, and water again
  2. dry with materialAfter drying (MgSO4)
  3. customthe solvent was removed in vacuo
  4. distillationdistilled

Sources & evidence

ORD record
ord-74e8ca400d9f4041b02c997c42da9c08
Source dataset
uspto-grants-1978_01
Patent number
US04071627

Reaction notes

Loading…