Triethylamine → HCID 54296393, compound

HRID 1633171Notes

Reaction equation

HRID 1633171 reaction equation
[S:1]([Cl:3])Cl.[CH3:4][NH:5][C:6](=[O:20])[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19].C(N(CC)CC)C>C(Cl)Cl>[Cl:3][S:1][N:5]([CH3:4])[C:6](=[O:20])[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25353Sulfur dichlorideHCID 3014113Carbamic acid, methyl-, dodecyl ester

Product 1

HCID 54296393HCID 54296393, compoundYield 101.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

To a solution of 62 g (0.6 mole) of sulfur dichloride in 200 ml of methylene chloride cooled to 0° C. under a nitrogen atmosphere was added a solution made up of 97.4 g (0.4 mole) of n-dodecyl N-methylcarbamate, 44.5 g (0.44 mole) of triethylamine and 150 ml of methylene chloride. The addition took 2.3 hr while the temperature was maintained at -10° to 5° C. After stirring for one additional hour at 5° C. the mixture was filtered under a positive nitrogen atmosphere, and the filtrate was concentrated. Triethylamine hydrochloride was removed by extracting the product into 200 ml of hexane. After filtration, the hexane solution was concentrated to give 125.6 g n-dodecyl N-chlorothio-N-methylcarbamate.

Workup

  1. additionwas added a solution
  2. additionThe addition
  3. temperaturewas maintained at -10° to 5° C
  4. filtrationwas filtered under a positive nitrogen atmosphere
  5. concentrationthe filtrate was concentrated
  6. customTriethylamine hydrochloride was removed
  7. extractionby extracting the product into 200 ml of hexane
  8. filtrationAfter filtration
  9. concentrationthe hexane solution was concentrated

Sources & evidence

ORD record
ord-0dc66afc7dd345949b1f31794dbd0686
Source dataset
uspto-grants-1984_10
Patent number
US04479002

Reaction notes

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