Sodium Hydroxide → 4-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-benzenesulfonyl chloride

HRID 1072504Notes

Reaction equation

HRID 1072504 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[Cl:20][S:21](O)(=[O:23])=[O:22].[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[C:10]([Cl:12])[CH:11]=1)[CH2:8][N:7]([CH3:13])[CH2:6][CH:5]2[C:14]1[CH:15]=[CH:16][C:17]([S:21]([Cl:20])(=[O:23])=[O:22])=[CH:18][CH:19]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 24638Chlorosulfonic acidHCID 223868076,8-Dichloro-2-methyl-4-phenyl-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 223868894-(6,8-Dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)-benzenesulfonyl chloride

Procedure

At 0° C., 1 mmol of 6,8-dichloro-2-methyl-4-phenyl-1,2,3,4-tetrahydro-isoquinoline (intermediate 4, example 2) was introduced into 1 ml of chlorosulfonic acid and stirred at room temperature for 3 hours. For workup, the reaction mixture was poured onto ice, adjusted to pH 7 to 8 with 1 N NaOH and extracted twice with ethyl acetate. The combined ethyl acetate phases were dried with Na2SO4 and concentrated in a rotary evaporator. The crude product obtained in this way was reacted further without further purification.

Workup

  1. additionFor workup, the reaction mixture was poured onto ice
  2. extractionextracted twice with ethyl acetate
  3. dry with materialThe combined ethyl acetate phases were dried with Na2SO4
  4. concentrationconcentrated in a rotary evaporator

Sources & evidence

ORD record
ord-b5527766ea1c482ea57f4e657c7feeaa
Source dataset
uspto-grants-2005_06
Patent number
US06911453B2

Reaction notes

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