Chloroform → N-methylisoquinoline-5-sulfonamide

HRID 638370Notes

Reaction equation

HRID 638370 reaction equation
[CH:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6]([S:11](Cl)(=[O:13])=[O:12])[C:5]=2[CH:4]=[CH:3][N:2]=1.[CH2:15]([N:17](CC)CC)C.Cl.CN.C(Cl)(Cl)Cl>ClCCl>[CH3:15][NH:17][S:11]([C:6]1[C:5]2[CH:4]=[CH:3][N:2]=[CH:1][C:10]=2[CH:9]=[CH:8][CH:7]=1)(=[O:13])=[O:12]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 33716555-Isoquinolinesulfonyl chlorideHCID 6364545Methylamine hydrochloride

Product 1

HCID 13135510N-methylisoquinoline-5-sulfonamideYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 50 ml of dichloromethane was dissolved 1.73 g of 5-isoquinolinesulfonyl chloride, and to the solution were added 1.54 g of triethylamine and 8.0 g of monomethylamine hydrochloride. The mixture was stirred at a temperature of 10° C. to 15° C. for 18 hours. The reaction solution obtained was washed with water, dried with magnesium sulfate, and then the dichloromethane was distilled therefrom under reduced pressure. The residue obtained was subjected to a silica gel column chromatography (silica: 50 g; solvent: chloroform) to give 1.30 g of N-methyl-5-isoquinolinesulfonamide, i.e., Compound (25) in a yield of 77%.

Workup

  1. customThe reaction solution obtained
  2. washwas washed with water
  3. dry with materialdried with magnesium sulfate
  4. distillationthe dichloromethane was distilled
  5. customThe residue obtained

Sources & evidence

ORD record
ord-b84c6db0d3a9488ab8fdf835ec3003c3
Source dataset
uspto-grants-1985_12
Patent number
US04560755

Reaction notes

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