Chlorosulfonic acid → 3-acetyl-7-chlorosulfonyl-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 621434Notes

Reaction equation

HRID 621434 reaction equation
[C:1]([N:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([O:15][CH3:16])=[CH:14][C:7]=2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[Cl:17][S:18](O)(=[O:20])=[O:19]>>[C:1]([N:4]1[CH2:5][CH2:6][C:7]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:11][C:8]=2[CH2:9][CH2:10]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 138533493-acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Product 1

HCID 138533503-acetyl-7-chlorosulfonyl-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine

Procedure

3-Acetyl-7-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine (2.3 g, 0.01 m) was added to chlorosulfonic acid (6 ml) which was stirred at 0°; the mixture was allowed to warm to 25° and stirred for 16 hours. The reaction was carefully poured into ice water and extracted with methylene chloride. The methylene chloride extracts were combined, washed, dried with magnesium sulfate and concentrated in vacuo to give 3-acetyl-7-chlorosulfonyl-8-methoxy-2,3,4,5-tetrahydro-1H-3-benzazepine, m.p. 153°-160°.

Workup

  1. temperatureto warm to 25°
  2. stirringstirred for 16 hours
  3. extractionextracted with methylene chloride
  4. washwashed
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9902e1c84c54472593c030c86f299233
Source dataset
uspto-grants-1989_04
Patent number
US04824839

Reaction notes

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