Dichloromethane → HCID 12799217, compound

HRID 1447118Notes

Reaction equation

HRID 1447118 reaction equation
[FH:1].C(Cl)Cl.[CH3:5][N:6]=[C:7]=[O:8].[CH2:9]([N:11]([CH2:14][CH3:15])[S:12]Cl)[CH3:10]>C(N(CC)CC)C>[CH3:5][N:6]([S:12][N:11]([CH2:14][CH3:15])[CH2:9][CH3:10])[C:7]([F:1])=[O:8]

Participants

6

Reactant 4

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

Product 1

HCID 12799217HCID 12799217, compoundYield 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-(diethylaminosulfenyl)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-8eda743ea2b64d51a28c7ad6b49a501c
Source dataset
uspto-grants-1982_02
Patent number
US04315928

Reaction notes

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