Dichloromethane → HCID 12838040, compound

HRID 1447114Notes

Reaction equation

HRID 1447114 reaction equation
[Cl:1][S:2]([OH:5])(=O)=[O:3].[C:6]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([Cl:19])[CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(=[O:8])[CH3:7].C(Cl)Cl>C(Cl)(Cl)Cl>[C:6]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[C:12]([Cl:19])[CH:13]=[CH:14][C:15]=2[S:2]([Cl:1])(=[O:5])=[O:3])[CH2:10]1)(=[O:8])[CH3:7]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24638Chlorosulfonic acidHCID 12838038HCID 12838038, compound

Product 1

HCID 12838040HCID 12838040, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

51.75 ml. (0.78 mole) of chlorosulfonic acid was added dropwise with stirring to a solution of 20.7 g. (0.099 mole) 2-acetyl-8-chloro-1,2,3,4-tetrahydroisoquinoline in 25 ml. of methylene chloride at -70° C. To effectuate a solution of the reactants 10 ml. of dry chloroform was added and the reaction mixture stirred for one hour at -70° C. The reaction mixture was then refluxed at 40°-45° C. for 2 hours and then stirred at ambient temperature for about 16 hours. The reaction mixture was then cautiously poured onto one liter of ice. The crude reaction product was then extracted into methylene chloride (3×100 ml.), washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated to dryness at reduced pressure to afford 2-acetyl-8-chloro-5-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline as whitish yellow solid with a melting point of 105°-115° C.

Workup

  1. customat -70° C
  2. stirringthe reaction mixture stirred for one hour at -70° C
  3. temperatureThe reaction mixture was then refluxed at 40°-45° C. for 2 hours
  4. stirringstirred at ambient temperature for about 16 hours
  5. customThe crude reaction product
  6. extractionwas then extracted into methylene chloride (3×100 ml.)
  7. washwashed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated to dryness at reduced pressure

Sources & evidence

ORD record
ord-4770d2cc023d4b8a87042a08acb9c7db
Source dataset
uspto-grants-1982_02
Patent number
US04315935

Reaction notes

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