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

HRID 561332Notes

Reaction equation

HRID 561332 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-62018bb200524cfc8d03c98cd4063498
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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