Chloroform → N-Butyl-5-isoquinolinesulfonamide

HRID 1263330Notes

Reaction equation

HRID 1263330 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.C(=O)([O-])[O-].[K+].[K+].[CH2:21]([NH2:25])[CH2:22][CH2:23][CH3:24].C(Cl)(Cl)Cl>ClCCl>[CH2:21]([NH:25][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])[CH2:22][CH2:23][CH3:24]

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8007ButylamineHCID 11430Potassium CarbonateHCID 33716555-Isoquinolinesulfonyl chloride

Product 1

HCID 13135514N-Butyl-5-isoquinolinesulfonamideYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of dichloromethane was dissolved 2.28 g of 5-isoquinolinesulfonyl chloride, and to the solution were added 1.38 g of anhydrous potassium carbonate and 1.46 g of n-butylamine, and the mixture thus obtained was stirred at a temperature of 20° C. to 25° C. for 12 hours. The reaction solution was washed with water, dried with anhydrous magnesium sulfate, and the dichloromethane was distilled therefrom under reduced pressure. The residue thus obtained was subjected to a silica gel column chromatography (silica gel: 70 g; solvent: chloroform) to give 1.90 g of N-n-butyl-5-isoquinolinesulfonamide, i.e., Compound (27) in a yield of 72%.

Workup

  1. customthe mixture thus obtained
  2. washThe reaction solution was washed with water
  3. dry with materialdried with anhydrous magnesium sulfate
  4. distillationthe dichloromethane was distilled
  5. customThe residue thus obtained

Sources & evidence

ORD record
ord-d77cf2ea70e8417f84289fac359e23e2
Source dataset
uspto-grants-1984_06
Patent number
US04456757

Reaction notes

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