Tetrahydrofuran → 2-(2-Chloro-1-chloromethyl-ethoxy)-6-(naphthalene-1-sulfonylmethyl)-phenylamine

HRID 33108Notes

Reaction equation

HRID 33108 reaction equation
[Cl:1][CH2:2][CH:3]([CH2:28][Cl:29])[O:4][C:5]1[C:6]([N+:25]([O-])=O)=[C:7]([CH2:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH:8]=[CH:9][CH:10]=1.C1COCC1>[Pd].CO>[Cl:29][CH2:28][CH:3]([CH2:2][Cl:1])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][S:12]([C:15]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=[CH:17][CH:16]=2)(=[O:13])=[O:14])[C:6]=1[NH2:25]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 597964381-[3-(2-Chloro-1-chloromethyl-ethoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene

Product 1

HCID 597964392-(2-Chloro-1-chloromethyl-ethoxy)-6-(naphthalene-1-sulfonylmethyl)-phenylamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[3-(2-chloro-1-chloromethyl-ethoxy)-2-nitro-phenylmethanesulfonyl]-naphthalene (3) (2.4 g, 5.3 mmoles) and 10% Pd/C in a 1:1 mixture of THF and methanol was hydrogenated on a Parr hydrogenator at 40 lb/in2 for 20 hours. The mixture was filtered through Celite. The filtrate was diluted with EtOAc, washed with water, dried over Na2SO4, and concentrated under vacuum to afford the title compound as an off white solid (2.02 g, 4.77 mmoles), identified by HNMR analysis.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. additionThe filtrate was diluted with EtOAc
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b07f7d877af1452ca4c32d8926e06992
Source dataset
uspto-grants-2008_09
Patent number
US07429582B2

Reaction notes

Loading…