Methanol → HCID 20572512, compound

HRID 895016Notes

Reaction equation

HRID 895016 reaction equation
FC(F)(F)C(N)=O.[Cl:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:25]=[CH:24][C:23]([S:26](=[O:31])(=[O:30])[N:27]([CH3:29])[CH3:28])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:32][CH2:33][O:34][C:10]=12.CO.[OH-].[Na+]>O>[Cl:8][C:9]1[C:19]2[CH2:18][CH2:17][NH:16][CH2:15][CH:14]([C:20]3[CH:21]=[CH:22][C:23]([S:26](=[O:30])(=[O:31])[N:27]([CH3:28])[CH3:29])=[CH:24][CH:25]=3)[C:13]=2[CH:12]=[C:11]2[O:32][CH2:33][O:34][C:10]=12

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 20572540HCID 20572540, compound

Product 1

HCID 20572512HCID 20572512, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2.3 g (0.00457 mole) of 6-chloro-7,8-methylenedioxy-1-(p-N,N-dimethylsulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide, 75 ml of methanol and 0.5 g of sodium hydroxide was stirred at room temperature for 2 hours, diluted with water and extracted several times with ethyl acetate. The extracts were washed with brine, dried and concentrated. The crude residue was chromatographed on 75 g of silica gel with a gradient of 1% to 4% of methanol in chloroform. The homogeneous cuts were combined and concentrated to give 1.4 g (75%) of 6-chloro-7,8-methylenedioxy-1-(p-N,N,-dimethylsulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine. A field description mass spectrogram showed an intense peak for m/e of 408 which is consistent with the structure. NMR and IR spectra also agreed with the structure.

Workup

  1. extractionextracted several times with ethyl acetate
  2. washThe extracts were washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe crude residue was chromatographed on 75 g of silica gel with a gradient of 1% to 4% of methanol in chloroform
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6b6798ef58e54c5693f0eb82e3438b86
Source dataset
uspto-grants-1981_08
Patent number
US04285938

Reaction notes

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