Triethylamine → HCID 20441850, compound

HRID 1633172Notes

Reaction equation

HRID 1633172 reaction equation
[FH:1].[CH3:2][N:3]=[C:4]=[O:5].Cl[S:7][N:8]([CH3:24])[C:9](=[O:23])[O:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C>C(Cl)Cl.O>[CH2:11]([O:10][C:9]([N:8]([CH3:24])[S:7][N:3]([CH3:2])[C:4]([F:1])=[O:5])=[O:23])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12228Methyl IsocyanateHCID 14917Hydrofluoric AcidHCID 54296393HCID 54296393, compound

Product 1

HCID 20441850HCID 20441850, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

Anhydrous hydrogen fluoride (8 g, 0.4 mole) was added to 400 ml of methylene chloride at 0° C. in a polyethylene reactor. Methylisocyanate (22.8 g, 0.4 mole) was added at -5° C. to 0° C. in 0.5 hr. After stirring for 1 hr at 0° C., a solution of 125.6 g of n-dodecyl N-chlorothio-N-methylcarbamate in 100 ml of methylene chloride was added, followed by a dropwise addition of 40.5 g (0.4 mole) of triethylamine. The mixture was stirred at 0° C. for one hour and was allowed to warm to ambient temperature. Water (300 ml) was added with vigorous stirring. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate, then with water until the washings became neutral, dried over anhydrous magnesium sulfate, filtered and concentrated to give 129 g (92%) of oily N-(N'-n-Dodecyloxycarbonyl-N'-Methylaminosulfenyl)-N-methylcarbamoyl fluoride.

Workup

  1. stirringThe mixture was stirred at 0° C. for one hour
  2. temperatureto warm to ambient temperature
  3. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9c695539bc0f4e27a7f27d8ddd78a3b6
Source dataset
uspto-grants-1984_10
Patent number
US04479002

Reaction notes

Loading…