Pyridine → N-(1-Methoxy-6-phenyl-6H-benzo[c]chromen-8-yl)-methanesulfonamide

HRID 1358118Notes

Reaction equation

HRID 1358118 reaction equation
[NH2:1][C:2]1[CH:23]=[CH:22][C:5]2[C:6]3[C:19]([O:20][CH3:21])=[CH:18][CH:17]=[CH:16][C:7]=3[O:8][CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:4]=2[CH:3]=1.N1C=CC=CC=1.[CH3:30][S:31](Cl)(=[O:33])=[O:32]>C(Cl)(Cl)Cl>[CH3:21][O:20][C:19]1[C:6]2[C:5]3[CH:22]=[CH:23][C:2]([NH:1][S:31]([CH3:30])(=[O:33])=[O:32])=[CH:3][C:4]=3[CH:9]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[O:8][C:7]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 181892091-Methoxy-6-phenyl-6H-benzo[c]chromen-8-ylamine

Product 1

HCID 10271193N-(1-Methoxy-6-phenyl-6H-benzo[c]chromen-8-yl)-methanesulfonamideYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

The solution of Example 5F (200 mg. 0.66 mmole), pyridine (300 mg) and methanesulfonyl chloride (227 mg., 2.00 mmole) in chloroform (3 mL) was stirred for 1 hour, washed with aqueous HCl (1M), dried (Na2SO4), filtered and concentrated under reduced pressure. Toluene was added and then concentrated. Heptane was added and concentrated under reduces pressure to provide the titled compound (199 mg. 80%). 1H NMR (300 MHz, CDCl3) δ 2.95 (s, 3H), 3.94 (s, 3H), 6.00 (s, 1H), 6.30 (s, 1H), 6.61 (d, J=2 Hz, 1H), 6.62 (dd, J=10 Hz, 2 Hz, 1H), 6.69 (dd, J=9 Hz, 1 Hz, 1H), 7.15 (t, J=9 Hz, 1H), 7.25 (dd, J=9 Hz, 2 Hz, 1H), 7.32-7.39 (m, 5H), 8.45 (d, J=9 Hz, 1H); MS (APCI) m/e 382 (M+H), 399 (M+NH4).

Workup

  1. washwashed with aqueous HCl (1M)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. additionToluene was added
  6. concentrationconcentrated
  7. additionHeptane was added
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-03f639fb1f3949ff9499c261a4ab355b
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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