Triethylamine → Naphthalene-1-sulfonic acid [5-(3-nitro-phenoxy)-pentyl]-amide

HRID 599182Notes

Reaction equation

HRID 599182 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])([O-:3])=[O:2].[C:17]1([S:27](Cl)(=[O:29])=[O:28])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C(N(CC)CC)C>ClCCl>[N+:1]([C:4]1[CH:5]=[C:6]([CH:14]=[CH:15][CH:16]=1)[O:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][S:27]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:29])=[O:28])([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 665601-Naphthalenesulfonyl chlorideHCID 690096135-(3-Nitro-phenoxy)-pentylamine

Product 1

HCID 86625271Naphthalene-1-sulfonic acid [5-(3-nitro-phenoxy)-pentyl]-amideYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(3-nitro-phenoxy)-pentylamine (336 mg, 1.5 mmol) and naphthalene-1-sulfonyl chloride (340 mg, 1.5 mmol) in dichloromethane (10 mL) was added triethylamine (182 mg, 1.8 mmol), and the resulting mixture was stirred at room temperature overnight. The reaction mixture was quenched with saturated ammonium chloride (30 mL) followed by extraction with ethyl acetate (10 mL×3). The organic layers were combined, washed with brine, and then concentrated under vacuum. The residue was subjected to column chromatography on silica gel to give naphthalene-1-sulfonic acid [5-(3-nitro-phenoxy)-pentyl]-amide (600 mg, 1.45 mmol, 97%) as a yellow liquid.

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride (30 mL)
  2. extractionfollowed by extraction with ethyl acetate (10 mL×3)
  3. washwashed with brine
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-4e1f6be0cedb4e5ca9b948008174f799
Source dataset
uspto-grants-2011_03
Patent number
US07897764B2

Reaction notes

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