Chlorosulfonic acid → 2-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

HRID 903561Notes

Reaction equation

HRID 903561 reaction equation
[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2].[Cl:14][S:15](O)(=[O:17])=[O:16]>>[C:1]([N:4]1[CH2:13][CH2:12][C:11]2[C:6](=[CH:7][C:8]([S:15]([Cl:14])(=[O:17])=[O:16])=[CH:9][CH:10]=2)[CH2:5]1)(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 6002152-Acetyl-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 126069042-Acetyl-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Conditions

Temperature
25 °C

Procedure

N-Acetyl-1,2,3,4-tetrahydroisoquinoline (180 gm., 1.03 m.) was added slowly to 800 gms. (6.9 m.) of chlorosulfonic acid and stirred at -50° C. The solution was stirred at 25° C. for two days, poured onto crushed ice and extracted with ethyl acetate. The extract was washed, dried over anhydrous sodium sulfate and evaporated to yield crude N-acetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline.

Workup

  1. additionpoured
  2. customonto crushed ice
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated

Sources & evidence

ORD record
ord-ac3a5073eeba45afae1730de4844130e
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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