P-Anisidine → HCID 59718039, compound

HRID 1726512Notes

Reaction equation

HRID 1726512 reaction equation
[C:1]([NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH:12]=[CH:13][CH:14]=[C:15]2[S:20](Cl)(=[O:22])=[O:21])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([NH2:39])=[CH:35][CH:34]=1>ClCCl>[CH3:31][O:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][S:20]([C:15]2[CH:14]=[CH:13][CH:12]=[C:11]3[C:16]=2[CH:17]=[CH:18][CH:19]=[C:10]3[NH:9][C:1](=[O:8])[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)(=[O:22])=[O:21])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 8471TriethylamineHCID 59717988HCID 59717988, compound

Product 1

HCID 59718039HCID 59718039, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-benzoylamino-naphthalene-1-sulfonyl chloride 44 (0.1 g, 0.29 mmol) in dichloromethane (0.5 mL) was added triethylamine (0.06 ml, 0.43 mmol) and p-anisidine (0.05 g, 0.3 mmol). The resultant solution stirred at room temperature for 3 hours. The reaction mixture was quenched with water and the compound extracted into ethyl acetate. The organic extracts were washed with brine, dried over MgSO4, filtered and concentrated to provide the crude product as a yellow oil. 1H NMR (300 MHz, DMSO) δ 8.65 (d, 1H), 8.19 (d, 1H), 8.06 (m, 3H), 7.70 (m, 2H), 7.54 (m, 2H), 6.84 (d, 2H), 6.69 (d, 2H), 3.56 (s, 3H); LC/MS (M+H)+ m/z 433.

Workup

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

Sources & evidence

ORD record
ord-4a940866d254437aacb4543263077f80
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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