Chlorosulfonic acid → 2-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

HRID 903570Notes

Reaction equation

HRID 903570 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[Cl:17][S:18](O)(=[O:20])=[O:19]>C(Cl)(Cl)Cl>[F:16][C:2]([F:1])([F:15])[C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9]([S:18]([Cl:17])(=[O:20])=[O:19])=[CH:10][CH:11]=2)[CH2:6]1)=[O:4]

Participants

4

Reactant 2

HCID 24638Chlorosulfonic acidHCID 6152162-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 113249022-(Trifluoroacetyl)-1,2,3,4-tetrahydroisoquinoline-7-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-trifluoroacetyl-1,2,3,4-tetrahydroisoquinoline 45.84 g. (0.2 mole) in 300 ml. of chloroform was added slowly 82.4 ml. (1.24 mole) of chlorosulfonic acid. The solution was stirred and the temperature allowed to come down to 25° C. The solution was quenched in ice water and extracted with chloroform. The extract was washed with water and dried over magnesium sulfate and concentrated. The residue was treated with ether and allowed to stand overnight. The resultant solid was filtered off, added to chloroform, cooled, treated with ether and allowed to stand in the cold for several hours. The resultant solid was again taken up in chloroform and treated with ether to give 2-trifluoroacetyl-7-chlorosulfonyl-1,2,3,4-tetrahydroisoquinoline, m.p. 108°-109° C.

Workup

  1. customto come down to 25° C
  2. customThe solution was quenched in ice water
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated
  7. additionThe residue was treated with ether
  8. filtrationThe resultant solid was filtered off
  9. additionadded to chloroform
  10. temperaturecooled
  11. additiontreated with ether
  12. customcold for several hours
  13. additiontreated with ether

Sources & evidence

ORD record
ord-76373ad855734e57b36d32e928023424
Source dataset
uspto-grants-1980_10
Patent number
US04228170

Reaction notes

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