Pyridine → (1-Methoxy-6-phenyl-6h-dibenzo(b,d)pyran-8-yl)benzenesulfonamide

HRID 1358119Notes

Reaction equation

HRID 1358119 reaction equation
N[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.[N:24]1C=CC=CC=1.[C:30]1([S:36](Cl)(=[O:38])=[O:37])[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C(Cl)(Cl)Cl>[CH3:21][O:20][C:19]1[C:6]2[C:5]3[CH:22]=[CH:23][C:2]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=4[S:36]([NH2:24])(=[O:38])=[O:37])=[CH:3][C:4]=3[CH:9]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[O:8][C:7]=2[CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 181892091-Methoxy-6-phenyl-6H-benzo[c]chromen-8-ylamine

Product 1

HCID 18189445(1-Methoxy-6-phenyl-6h-dibenzo(b,d)pyran-8-yl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of Example 5F (50 mg. 0.16 mmole), pyridine (75 mg) and benzenesulfonyl chloride (86 mg., 0.5 mmole) in chloroform (1 mL) was stirred for 1 hour, washed with aqueous HCl (1M), dried (Na2SO4), filtered and concentrated under reduced pressure. The concentrate was purified by reverse-phase HPLC with CH3CN/water to provide the titled product. MS (ESI(−)Q1MS) m/z 442 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 10.38 (s, 1H), 8.22 (d, J=9 Hz, 1H), 7.70-7.50 (m, 5H), 7.36-7.29 (m, 3H), 7.16-7.06 (m, 4H), 6.76 (s, 1H), 6.69 (d, J=8 Hz, 1H), 6.62(d, J=8 Hz, 1H), 6.11 (s, 1H), 3.85 (s, 3H).

Workup

  1. washwashed with aqueous HCl (1M)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe concentrate was purified by reverse-phase HPLC with CH3CN/water

Sources & evidence

ORD record
ord-88e6f5f298084e2c9482c4bcb5455c30
Source dataset
uspto-grants-2003_07
Patent number
US06593480B2

Reaction notes

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