4-Toluenesulfonyl chloride → HCID 58812101, compound

HRID 2240015Notes

Reaction equation

HRID 2240015 reaction equation
[C:1]1([S:11]([CH2:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[N+:25]([O-:27])=[O:26])[O:18][CH2:19][CH2:20][OH:21])(=[O:13])=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:28]1([CH3:38])[CH:33]=[CH:32][C:31]([S:34](Cl)(=[O:36])=[O:35])=[CH:30][CH:29]=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]1([S:11]([CH2:14][C:15]2[CH:16]=[C:17]([CH:22]=[CH:23][C:24]=2[N+:25]([O-:27])=[O:26])[O:18][CH2:19][CH2:20][O:21][S:34]([C:31]2[CH:32]=[CH:33][C:28]([CH3:38])=[CH:29][CH:30]=2)(=[O:36])=[O:35])(=[O:12])=[O:13])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 588120652-[3-(Naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethanol

Product 1

HCID 58812101HCID 58812101, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethanol (14.3 g, 36.9 mmol), p-toluenesulfonylchloride (14.9 g, 78.2 mmol) and triethylamine (23 mL, 170 mmol) in methylene chloride (400 mL) was stirred under nitrogen at ambient temperature for 2 hours, 45 minutes. The reaction mixture was then concentrated and partitioned in methylene chloride and aqueous sodium bicarbonate. The organic phase was washed with brine, dried with anhydrous magnesium sulfate, filtered and concentrated. The residue was purified by flash chromatography with 25-75% ethyl acetate in hexane and 100% ethyl acetate. Drying for 25 minutes in vacuo at 80° C. yielded toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethyl ester as a rust-colored solid (15.7 g, 78.5%). Mass Spectrum (+EI, [M+H]+) m/z 542. 1HNMR (500 MHz, DMSO-d6): 88.53 (dd, 1H, J=8.18 Hz and 1.10 Hz), 8.31 (d, 1H, J=8.30 Hz), 8.09-8.11 (m, 1H), 7.94-7.99 (m, 2H), 7.62-7.75 (m, 5H), 7.42 (d, 2H, J=7.93 Hz), 6.98 (dd, 1H, J=9.15 Hz and 2.93 Hz), 6.80 (d, 1H, J=2.81 Hz), 5.20 (s, 2H), 4.28-4.30 (m, 2H), 4.10-4.12 (m, 2H), 2.37 ppm (s, 3H).

Workup

  1. concentrationThe reaction mixture was then concentrated
  2. custompartitioned in methylene chloride
  3. washThe organic phase was washed with brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography with 25-75% ethyl acetate in hexane and 100% ethyl acetate
  8. customDrying for 25 minutes in vacuo at 80° C.

Sources & evidence

ORD record
ord-b75c48f57a234f6ba94210bee0eda801
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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