Ethanol → Toluene-4-sulfonic acid 2-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-ethyl ester

HRID 2240016Notes

Reaction equation

HRID 2240016 reaction equation
C(O)C.[C:4]1([S:14]([CH2:17][C:18]2[CH:19]=[C:20]([CH:35]=[CH:36][C:37]=2[N+:38]([O-])=O)[O:21][CH2:22][CH2:23][O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:27])=[O:26])(=[O:16])=[O:15])[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1>[Pd].C1COCC1>[NH2:38][C:37]1[CH:36]=[CH:35][C:20]([O:21][CH2:22][CH2:23][O:24][S:25]([C:28]2[CH:33]=[CH:32][C:31]([CH3:34])=[CH:30][CH:29]=2)(=[O:26])=[O:27])=[CH:19][C:18]=1[CH2:17][S:14]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)(=[O:15])=[O:16]

Participants

5

Reactant 2

HCID 702EthanolHCID 58812101HCID 58812101, compound

Product 1

HCID 58812122Toluene-4-sulfonic acid 2-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-ethyl esterYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethanol (180 mL) and 10% palladium on carbon (5.2 g) were added to a hot solution of toluene-4-sulfonic acid 2-[3-(naphthalene-1-sulfonylmethyl)-4-nitro-phenoxy]-ethyl ester (11.5 g, 21.2 mmol) in THF (180 mL). This mixture was shaken on the Parr hydrogenation apparatus for 5 hours, with a starting pressure of 47 psi. It was then filtered over Celite, concentrated and dried in vacuo at 80° C. for 30 minutes to give toluene-4-sulfonic acid 2-[4-amino-3-(naphthalene-1-sulfonylmethyl)-phenoxy]-ethyl ester as a dark brown gum (9.5 g, 88.0%). Mass Spectrum (+EI, [M+H]+) m/z 512. 1HNMR (500 MHz, DMSO-d6): 88.61 (d, 1H, J=8.41 Hz), 8.25 (d, 1H, J=8.30 Hz), 8.03-8.08 (m, 2H), 7.59-7.75 (m, 5H), 7.43 (d, 2H, J=7.93 Hz), 6.49-6.53 (m, 2H), 6.11 (d, 1H, J=2.68 Hz), 4.65-4.77 (br, 2H), 4.59 (s, 2H), 4.09-4.11 (m, 2H), 3.63-3.65 (m, 2H), 2.38 ppm (s, 3H).

Workup

  1. filtrationIt was then filtered over Celite
  2. concentrationconcentrated
  3. customdried in vacuo at 80° C. for 30 minutes

Sources & evidence

ORD record
ord-49b1603fb8444d87ba5a2ce86dcf6aa7
Source dataset
uspto-grants-2010_05
Patent number
US07723329B2

Reaction notes

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