Triethylamine → N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}methanesulfonamide

HRID 1993002Notes

Reaction equation

HRID 1993002 reaction equation
[CH3:1][C:2]1[C:3]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[C:4]([O:14][C:15]2[CH:21]=[CH:20][C:18]([NH2:19])=[CH:17][CH:16]=2)[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([O:12][CH3:13])=[CH:7][CH:6]=2.CCN(CC)CC.[CH3:35][S:36](Cl)(=[O:38])=[O:37]>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:13][O:12][C:8]1[CH:9]=[C:10]2[C:5](=[CH:6][CH:7]=1)[C:4]([O:14][C:15]1[CH:21]=[CH:20][C:18]([NH:19][S:36]([CH3:35])(=[O:38])=[O:37])=[CH:17][CH:16]=1)=[C:3]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:2]([CH3:1])=[CH:11]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 685373984-{[3-Methyl-6-(methyloxy)-2-phenyl-1-naphthalenyl]oxy}aniline

Product 1

HCID 68536755N-{4-[(6-methoxy-3-methyl-2-phenyl-1-naphthalenyl)oxy]phenyl}methanesulfonamideYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a flask containing a solution of 29, Et3N (0.26 g, 2.55 mmol) and DMAP (0.032, 0.26 mmol) in CH2Cl2 (5 mL) was added methanesulfonyl chloride (0.24 g, 2.13 mmol), dropwise at RT and the reaction allowed to stir overnight. After 18 h the reaction was diluted with CH2Cl2 (15 mL) and the reaction rinsed with 10% aqueous HCl (25 mL). The CH2Cl2 layer was dried (MgSO4) and concentrated to a dark amber oil. The crude product was purified by silica gel column chromatography to afford 170 mg (46%) of the title compound (269) as a colorless oil. An additional 90 mg of a mixture of 269 and N,N-bissulfonylated product was also isolated. 1H NMR (400 MHz, DMSO-d6): δ 2.15 (s, 3H), 2.82 (s, 3H), 3.85 (s, 3H), 6.54 (d, J=8.9 Hz, 2H), 6.94 (d, J=8.8 Hz, 2H), 6.97 (dd, J1=2.4 Hz, J2=9.1 Hz, 1H), 6.96 (d, J=6.6 Hz, 1H), 7.15-7.32 (m, 5H), 7.58 (d, J=9.1 Hz, 1H), 7.67 (s, 1H), 9.32 (s, 1H).

Workup

  1. customdropwise at RT
  2. washthe reaction rinsed with 10% aqueous HCl (25 mL)
  3. dry with materialThe CH2Cl2 layer was dried (MgSO4)
  4. concentrationconcentrated to a dark amber oil
  5. customThe crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5719289afbed49e481497d7d472e972f
Source dataset
uspto-grants-2010_01
Patent number
US07649093B2

Reaction notes

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