Triethylamine → Methanesulfonic Acid [2-[(3,4-dichlorophenyl)thio]ethyl]ester

HRID 4191Notes

Reaction equation

HRID 4191 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][OH:12])[CH:5]=[CH:6][C:7]=1[Cl:8].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:10][CH2:11][O:12][S:21]([CH3:20])(=[O:23])=[O:22])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 27582053,4-Dichlorophenylthioethanol

Product 1

HCID 14050283Methanesulfonic Acid [2-[(3,4-dichlorophenyl)thio]ethyl]ester

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

To a solution of 117.97 g (0.53 mole) of 2-[(3,4-dichlorophenyl)thio]ethanol (prepared by reacting 3,4-dichlorothiophenol and 2-chloroethanol) and 53.5 g (0.53 mole) of triethylamine in 500 ml of benzene was added dropwise a benzene solution of 60.9 g (0.53 mole) of methanesulfonyl chloride over a one hour period with cooling in an ice bath. The reaction mixture was stirred at room temperature overnight and filtered. Solvent was removed from the filtrate in a rotary evaporator to give an oil which crystallized. A portion was recrystallized from isopropyl ether to give white crystalline solid, m.p. 53°-55° C.

Workup

  1. temperaturewith cooling in an ice bath
  2. filtrationfiltered
  3. customSolvent was removed from the filtrate in a rotary evaporator
  4. customto give an oil which
  5. customcrystallized
  6. customA portion was recrystallized from isopropyl ether
  7. customto give white crystalline solid, m.p. 53°-55° C.

Sources & evidence

ORD record
ord-cc9151e5ad6b4f33b85396bdbeeebe64
Source dataset
uspto-grants-1988_02
Patent number
US04724235

Reaction notes

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