Triethylamine → N-[4-(3-Methoxy-phenylsulfamoyl)-naphthalen-1-yl]-benzamide

HRID 561272Notes

Reaction equation

HRID 561272 reaction equation
[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](Cl)(=[O:22])=[O:21])=[CH:12][CH:11]=1)(=[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][CH:36]=[C:35]([NH2:39])[CH:34]=1>C(Cl)Cl>[CH3:31][O:32][C:33]1[CH:34]=[C:35]([NH:39][S:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:11][CH:12]=2)(=[O:22])=[O:21])[CH:36]=[CH:37][CH:38]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108243-MethoxyanilineHCID 161057574-Benzoylamino-naphthalene-1-sulfonyl chloride

Product 1

HCID 11305023N-[4-(3-Methoxy-phenylsulfamoyl)-naphthalen-1-yl]-benzamideYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-benzoylamino-naphthalene-1-sulfonyl chloride (320 mg, 0.93 mmol) in CH2Cl2 (20 mL) was added triethylamine (0.26 mL, 1.85 mmol) and m-anisidine (137 mg, 1.11 mmol). The resultant solution was stirred at 25° C. overnight. The reaction mixture was quenched with water and extracted with CH2Cl2. The organic extracts were combined, washed with brine, dried over Na2SO4, filtered and concentrated to provide the crude product as yellow viscous oil. HPLC purification of the residue gave the title compound (190 mg) as a pale white solid. 1H NMR (300 MHz, DMSO) δ 8.72 (d, 1H), 8.26 (d, 1H), 8.15 (d, 1H), 8.02 (d, 2H), 7.78 (d, 1H), 7.60 (m, 5H), 7.00 (t, 1H), 6.55 (m, 2H), 6.46 (d, 1H), 3.56 (s, 3H); LC/MS m/z 433 (M+H)+.

Workup

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto provide the crude product as yellow viscous oil
  8. customHPLC purification of the residue

Sources & evidence

ORD record
ord-371ae378513f48b8af939b784a5c2d45
Source dataset
uspto-grants-2011_11
Patent number
US08063222B2

Reaction notes

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