4-Toluenesulfonyl chloride → HCID 58812135, compound

HRID 2239987Notes

Reaction equation

HRID 2239987 reaction equation
[C:1]1([S:7]([CH2:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=2[N+:21]([O-:23])=[O:22])[O:14][CH2:15][CH2:16][OH:17])(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:7]([CH2:10][C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][C:20]=2[N+:21]([O-:23])=[O:22])[O:14][CH2:15][CH2:16][O:17][S:30]([C:27]2[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=2)(=[O:32])=[O:31])(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58812110HCID 58812110, compound

Product 1

HCID 58812135HCID 58812135, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(3-benzenesulfonylmethyl-4-nitro-phenoxy)-ethanol (8.2 g, 24 mmol), p-toluenesulfonyl chloride (9.39 g, 49.3 mmol) and triethylamine (19 mL, 140 mmol) in methylene chloride (85 mL) was stirred at ambient temperature under nitrogen for 4.5 hours. It then was solvent evaporated and partitioned in methylene chloride and aqueous sodium bicarbonate. The organic phase was then washed with brine, dried with anhydrous magnesium sulfate, filtered, concentrated and dried in vacuo at 63° C. for 30 minutes. The residue was purified by flash chromatography with 100% chloroform and 5% methanol in chloroform. It was dried in vacuo at 65° C. for 20 minutes to yield toluene-4-sulfonic acid 2-(3-benzenesulfonylmethyl-4-nitro-phenoxy)-ethyl ester as a yellow solid (8.1 g, 69%); Mass spectrum (−EI, [M−H]−) m/z 490. 1HNMR (300 MHz, DMSO-d6): δ7.99 (d, 1H, J=9.02 Hz), 7.67-7.75 (m, 3H), 7.54-7.62 (m, 4H), 7.43 (d, 2H, J=7.93 Hz), 7.00 (dd, 1H, J=9.15 Hz and 2.80 Hz), 6.78 (d, 1H, J=2.81 Hz), 5.09 (s, 2H), 4.29-4.31 (m, 2H), 4.13-4.15 (m, 2H), 2.37 ppm (s, 3H). Elemental Analysis for C22H21NO8S 0.40 mol H2O: Calcd: C, 52.98; H, 4.41; N, 2.81; Found: C, 52.67; H, 4.26; N, 2.61.

Workup

  1. customevaporated
  2. custompartitioned in methylene chloride
  3. washThe organic phase was then washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customdried in vacuo at 63° C. for 30 minutes
  8. customThe residue was purified by flash chromatography with 100% chloroform and 5% methanol in chloroform
  9. customIt was dried in vacuo at 65° C. for 20 minutes

Sources & evidence

ORD record
ord-f31692d763044f64b6054011173eb6bf
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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