Water → HCID 59770131, compound

HRID 2218658Notes

Reaction equation

HRID 2218658 reaction equation
[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([NH:23][S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:30]I.O>CN(C=O)C.C(OCC)(=O)C>[CH:1]1[C:11]2[CH2:10][CH2:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[CH:16][C:17]3[CH:18]=[C:19]([N:23]([CH3:30])[S:24]([CH3:27])(=[O:26])=[O:25])[CH:20]=[CH:21][CH:22]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59770003HCID 59770003, compound

Product 1

HCID 59770131HCID 59770131, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve N-[3-(10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide (10 mg, 0.265 mmol) in DMF (4 mL) and add NaH (13 mg of a 60% suspension in mineral oil, 0.318 mmol). Stir at room temperature for 50 min, then add MeI (33□L, 75 mg, 0.530 mmol). Stir at room temp for 1 h. Dilute reaction mixture with H2O and ethyl acetate. Separate layers, and wash organics with H2O. Dry organics (MgSO4) and concentrate to 101 mg (100%) of a pale yellow solid, mp 124.2° C. 1H NMR (CDCl3) δ 2.53 (s, 3H), 2.72-3.54 (br m, 4H), 6.74 (s, 1H), 6.78 (s, 1H), 6.91-7.43 (m, 11H); MS (ES) 412 (M+Na). HPLC shows 97% purity.

Workup

  1. stirringStir at room temp for 1 h
  2. additionDilute
  3. washSeparate layers, and wash organics with H2O
  4. concentrationDry organics (MgSO4) and concentrate to 101 mg (100%) of a pale yellow solid, mp 124.2° C

Sources & evidence

ORD record
ord-56244a876ffc43aab4491ffeedfbbbb0
Source dataset
uspto-grants-2008_08
Patent number
US07411072B2

Reaction notes

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