Triethylamine → 7-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride

HRID 1008525Notes

Reaction equation

HRID 1008525 reaction equation
[S:1]([Cl:5])(Cl)(=[O:3])=[O:2].Cl.[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][CH2:16]2)=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:7][O:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][N:15]([S:1]([Cl:5])(=[O:3])=[O:2])[CH2:16]2)=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 27521977-Methoxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

Product 1

HCID 226656767-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred, precooled solution (−40° C.) of 0.41 mL of sulfuryl chloride in 10 mL of chloroform was added a mixture of 1.0 g of 7-methoxy-1,2,3,4-tetrahydro-isoquinoline-hydrochloride and 2.1 mL of triethylamine in 25 mL of chloroform at −40° C. Stirring was continued at −30° C. for one hour and additionally at 5° C. for one hour. The mixture was poured on ice, the organic layer extracted with cold water, dried (sodium sulfate) and concentrated. The residue was redissolved in diethyl ether and chromatographed on silica gel (isohexane/ethyl acetate=8/2 v/v) yielding 0.62 g of 7-methoxy-3,4-dihydro-1H-isoquinoline-2-sulfonyl chloride as an oil.

Workup

  1. additionThe mixture was poured on ice
  2. extractionthe organic layer extracted with cold water
  3. dry with materialdried (sodium sulfate)
  4. concentrationconcentrated
  5. dissolutionThe residue was redissolved in diethyl ether
  6. customchromatographed on silica gel (isohexane/ethyl acetate=8/2 v/v)

Sources & evidence

ORD record
ord-28f0ba20540e439dbbefb1ca309d4fce
Source dataset
uspto-grants-2004_09
Patent number
US06797710B2

Reaction notes

Loading…