3,5-Dichlorobenzenesulfonyl chloride → 6-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid

HRID 1697271Notes

Reaction equation

HRID 1697271 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([S:9](Cl)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[NH2:13][C:14]1[CH:15]=[C:16]2[C:21](=[CH:22][CH:23]=1)[C:20]([C:24]([OH:26])=[O:25])=[CH:19][CH:18]=[CH:17]2>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([NH:13][C:14]2[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=2)[C:20]([C:24]([OH:26])=[O:25])=[CH:19][CH:18]=[CH:17]3)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 5223883,5-Dichlorobenzenesulfonyl chlorideHCID 234228256-Aminonaphthalene-1-carboxylic acid

Product 1

HCID 584969666-(3,5-Dichloro-phenylsulphonylamino)-naphthalene-1-carboxylic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2.68 g 3,5-dichloro-phenylsulphonyl chloride are added to 2.00 g of 6-amino-naphthalene-1-carboxylic acid in 10 ml of pyridine while cooling with an ice bath. The reaction mixture is left overnight to come up to ambient temperature and then the pyridine is distilled off in vacuo using the rotary evaporator. The flask residue is acidified with 3 N hydrochloric acid and extracted with ethyl acetate/methanol. The combined extracts are washed with water, dried on magnesium sulphate and evaporated down. The crude product is purified by chromatography through a silica gel column with cyclohexane/ethyl acetate (65:35 to 0:100) as eluant.

Workup

  1. temperaturewhile cooling with an ice bath
  2. customto come up to ambient temperature
  3. distillationthe pyridine is distilled off in vacuo
  4. customthe rotary evaporator
  5. extractionextracted with ethyl acetate/methanol
  6. washThe combined extracts are washed with water
  7. customdried on magnesium sulphate
  8. customevaporated down
  9. customThe crude product is purified by chromatography through a silica gel column with cyclohexane/ethyl acetate (65:35 to 0:100) as eluant

Sources & evidence

ORD record
ord-a0360b32f56345ee86f3c6f109474799
Source dataset
uspto-grants-2012_04
Patent number
US08163911B2

Reaction notes

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