5-Amino-1-naphthalenesulfonic acid → HCID 6611518, compound

HRID 2225126Notes

Reaction equation

HRID 2225126 reaction equation
[CH:1]1[CH:14]=[C:13]([NH2:15])[C:4]2[CH:5]=[CH:6][CH:7]=[C:8]([S:9]([OH:12])(=[O:11])=[O:10])[C:3]=2[CH:2]=1.C(N(CC)CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>ClCCl>[C:23]([NH:15][C:13]1[CH:14]=[CH:1][CH:2]=[C:3]2[C:4]=1[CH:5]=[CH:6][CH:7]=[C:8]2[S:9]([OH:12])(=[O:10])=[O:11])(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 67935-Amino-1-naphthalenesulfonic acidHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 6611518HCID 6611518, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To an ice cooled solution of 1-naphthylamine-5-sulfonic acid (2 g, 8.9 mmol) in dichloromethane (5 mL), was added triethylamine (1.87 mL, 13.4 mmol). Benzoyl chloride (1.14 ml, 9.85 mmol) was added and the resultant solution was stirred at room temperature overnight. The reaction mixture was quenched by pouring into ice water, and the product was extracted into ethyl acetate. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide crude intermediate 43 as a white solid that was used without further purification.

Workup

  1. customThe reaction mixture was quenched
  2. additionby pouring into ice water
  3. extractionthe product was extracted into ethyl acetate
  4. washThe organic extracts were washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-0ae10b67619c468e9416b62c652a3d82
Source dataset
uspto-grants-2008_05
Patent number
US07378525B2

Reaction notes

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