Chloroform → N-methylisoquinoline-5-sulfonamide

HRID 1248750Notes

Reaction equation

HRID 1248750 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-22a5c6595f8a4bef97d839057b8d7eab
Source dataset
uspto-grants-1985_06
Patent number
US04525589

Reaction notes

Loading…