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

HRID 1726510Notes

Reaction equation

HRID 1726510 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-4ea193ed3f834e4cbe2440f40fc66039
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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