Triethylamine → 4-methylsulfonamido-N-[2-[(1-methylethyl)amino]ethyl]benzene sulfonamide

HRID 2414196Notes

Reaction equation

HRID 2414196 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12](Cl)(=[O:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].[CH:16]([NH:19][CH2:20][CH2:21][NH2:22])([CH3:18])[CH3:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([NH:22][CH2:21][CH2:20][NH:19][CH:16]([CH3:18])[CH3:17])(=[O:14])=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 88098N-IsopropylethylenediamineHCID 134620384-Methanesulfonamidobenzene-1-sulfonyl chloride

Product 1

HCID 155993894-methylsulfonamido-N-[2-[(1-methylethyl)amino]ethyl]benzene sulfonamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-methylsulfonamidobenzenesulfonyl chloride (2.70 g) was added portionwise to a 0.01 mole portion of N-isopropylethylenediamine and triethylamine (0.01 mole) in methylene chloride (250 ml) to obtain a white solid which precipitated from the methylene chloride reaction mixture 2.62 g, m.r. 180°-182° C. This solid was washed well with methylene chloride, dissolved in isopropanol/HCl/methanol and the methanol boiled away. The product was precipitated and filtered to yield 1.65 g, m.r. 158°-160° C.(d).

Workup

  1. customto obtain a white solid which
  2. customprecipitated from the methylene chloride reaction mixture 2.62 g, m.r
  3. custom180°-182° C
  4. washThis solid was washed well with methylene chloride
  5. dissolutiondissolved in isopropanol/HCl/methanol
  6. customThe product was precipitated
  7. filtrationfiltered
  8. customto yield 1.65 g, m.r

Sources & evidence

ORD record
ord-b40dd9ce38bd46fd98ca1563909faf60
Source dataset
uspto-grants-1988_01
Patent number
US04721809

Reaction notes

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