Chlorosulfonic acid → HCID 20160682, compound

HRID 247440Notes

Reaction equation

HRID 247440 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([N:9]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[C:23]([O:26][CH3:27])[CH:24]=[CH:25][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[CH3:7]>C(Cl)Cl>[C:6]([N:9]1[CH2:15][CH:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:13]2[CH:22]=[C:23]([O:26][CH3:27])[C:24]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:25][C:12]=2[CH2:11][CH2:10]1)(=[O:8])[CH3:7]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 20160738HCID 20160738, compound

Product 1

HCID 20160682HCID 20160682, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Chlorosulfonic acid (2.3 g, 0.02 m) dissolved in methylene chloride (50 ml) was added slowly to a solution of 3-acetyl-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine (2.95 g, 0.01 m) in methylene chloride (100 ml) stirred at -20°. The mixture was stirred at -20° for thirty minutes, and allowed to warm to 25°. The methylene chloride was decanted and the insoluble residue was treated with excess thionyl chloride in chloroform, heated to reflux, cooled and poured into ice water. The mixture was extracted with chloroform and the organic layer was washed, dried with sodium sulfate and concentrated in vacuo to give 3-acetyl 7-chlorosulfonyl-8-methoxy-1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepine.

Workup

  1. stirringThe mixture was stirred at -20° for thirty minutes
  2. temperatureto warm to 25°
  3. customThe methylene chloride was decanted
  4. additionthe insoluble residue was treated with excess thionyl chloride in chloroform
  5. temperatureheated
  6. temperatureto reflux
  7. temperaturecooled
  8. additionpoured into ice water
  9. extractionThe mixture was extracted with chloroform
  10. washthe organic layer was washed
  11. dry with materialdried with sodium sulfate
  12. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-ee920fdb026a4dd4a72a552cdfbea98c
Source dataset
uspto-grants-1987_11
Patent number
US04707483

Reaction notes

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