Triethylamine → HCID 13367235, compound

HRID 1633173Notes

Reaction equation

HRID 1633173 reaction equation
[S:1]([Cl:3])Cl.[CH3:4][NH:5][C:6](=[O:16])[O:7][CH2:8][CH:9]([CH2:14][CH3:15])[CH2:10][CH2:11][CH2:12][CH3:13].C(N(CC)CC)C>C(Cl)Cl>[Cl:3][S:1][N:5]([CH3:4])[C:6](=[O:16])[O:7][CH2:8][CH:9]([CH2:14][CH3:15])[CH2:10][CH2:11][CH2:12][CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 25353Sulfur dichlorideHCID 13367245HCID 13367245, compound

Product 1

HCID 13367235HCID 13367235, compoundYield 103.8%

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 of 75 g (0.4 mole) of 2-ethylhexyl N-methylcarbamate and 44.5 g (0.44 mole) of triethylamine in 100 ml of methylene chloride at -10° to 3° C. The addition took 2 hr. After stirring for 1 hr at 5° C., the mixture was filtered under a positive nitrogen atmosphere, and the filtrate was concentrated. The product was extracted into 200 ml of hexanes and the solid triethylamine hydrochloride was filtered. The filtrate was concentrated to give 105.4 g of 2-ethylhexyl N-chlorothio-N-methylcarbamate.

Workup

  1. additionThe addition
  2. filtrationthe mixture was filtered under a positive nitrogen atmosphere
  3. concentrationthe filtrate was concentrated
  4. extractionThe product was extracted into 200 ml of hexanes
  5. filtrationthe solid triethylamine hydrochloride was filtered
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0e4fa69f3ebe46d99984e9bb6bab2ccf
Source dataset
uspto-grants-1984_10
Patent number
US04479002

Reaction notes

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