Triethylamine → 2-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoate

HRID 2182906Notes

Reaction equation

HRID 2182906 reaction equation
[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].S(Cl)(Cl)=O.[C:18]1([CH3:30])[CH:23]=[CH:22][C:21]([S:24]([CH2:27][CH2:28]O)(=[O:26])=[O:25])=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[Cl:1][S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([O:10][CH2:28][CH2:27][S:24]([C:21]1[CH:22]=[CH:23][C:18]([CH3:30])=[CH:19][CH:20]=1)(=[O:26])=[O:25])=[O:9])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-2×HCID 89682Ethanol, 2-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 224793682-(4-Methylbenzene-1-sulfonyl)ethyl 3-(chlorosulfonyl)benzoateYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(chlorosulfonyl) benzoic acid (Intermediate 73, 5.51 g, 0.025 mol) and thionyl chloride (17.85 g, 11 mL, 0.15 mol) was refluxed for 1 hr. Excess thionyl chloride was distilled off at atmospheric pressure and finally at reduced pressure to give crude acid chloride. To a mixture of the crude acid chloride and 2-(p-tolylsulfonyl)ethanol (4.8 g, 0.024 mol) in dichloromethane (50 mL) was added triethylamine (2.52 g, 0.025 mol) at room temperature. TLC showed the reaction mixture was complete after 1 hr. The reaction mixture was washed with water (2×25 mL), filtered through 1PS filter paper and concentrated under reduced pressure to give 10 g of a viscous oil. The oil was purified by flash chromatography (silica gel, 25 to 50% ethyl acetate in hexane) to give 6.1 g (63%) of the title compound as a white solid.

Workup

  1. temperaturewas refluxed for 1 hr
  2. distillationExcess thionyl chloride was distilled off at atmospheric pressure and finally at reduced pressure
  3. customto give crude acid chloride
  4. washThe reaction mixture was washed with water (2×25 mL)
  5. filtrationfiltered through 1PS filter paper
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5bae3a26afbb424398a66050da975855
Source dataset
uspto-grants-2005_05
Patent number
US06897227B2

Reaction notes

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