Thionyl Chloride → HCID 86737970, compound

HRID 895014Notes

Reaction equation

HRID 895014 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[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)(=[O:28])=[O:27])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12.S(Cl)(Cl)=O>CN(C)C=O>[F:1][C:2]([F:7])([F:6])[C:3]([NH2:5])=[O:4].[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:28])(=[O:27])[NH2:5])=[CH:22][CH:21]=3)[C:13]=2[CH:12]=[C:11]2[O:30][CH2:31][O:32][C:10]=12

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 86737971HCID 86737971, compound

Product 1

HCID 86737970HCID 86737970, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 1.0 g (2.1 mmole) of the crude 6-chloro-7,8-methylenedioxy-1-(p-sulfophenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide, 20 ml of thionyl chloride and 0.04 ml of dimethylformamide was heated at 80° for 2 hours. The thionyl chloride was evaporated in vacuo. The residue which is 6-chloro-7,8-methylenedioxy-1-(p-chlorosulfonylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide was dissolved in tetrahydrofuran. The solution was added slowly to 40 ml of iced concentrated ammonium hydroxide. The mixture was stirred at room temperature for an hour, the pH was adjusted to 8 with hydrochloric acid and the product was extracted into ethyl acetate. The extracts were washed with water, dried, concentrated and applied to a column packed with 50 g of silica gel. The column was developed with a gradient of 24 to 35 percent of ethyl acetate in cyclohexane to give 0.5 g of 6-chloro-7,8-methylenedioxy-1-(p-sulfamylphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine trifluoroacetamide. Field desorption mass spectroscopy showed an intense m/e at 476 which is consistent with the molecular ion. NMR and IR were consistent with the structure.

Workup

  1. temperaturewas heated at 80° for 2 hours
  2. customThe thionyl chloride was evaporated in vacuo
  3. dissolutionwas dissolved in tetrahydrofuran
  4. additionThe solution was added slowly to 40 ml of iced concentrated ammonium hydroxide
  5. extractionthe product was extracted into ethyl acetate
  6. washThe extracts were washed with water
  7. customdried
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-71ffae48cc0e415b92c93460b08f51d7
Source dataset
uspto-grants-1981_08
Patent number
US04285938

Reaction notes

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