[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]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).
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