Triethylamine → N-[4-[[(1-Methylethyl)-[2-[(1-methylethyl)amino]ethyl]amino]sulfonyl]phenyl]acetamide

HRID 255680Notes

Reaction equation

HRID 255680 reaction equation
[NH:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11](Cl)(=[O:13])=[O:12])=[CH:7][CH:6]=1)[C:2]([CH3:4])=[O:3].[CH:15]([NH:18][CH2:19][CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])([CH3:17])[CH3:16].C(N(CC)CC)C>C(Cl)Cl>[CH3:16][CH:15]([N:18]([CH2:19][CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[S:11]([C:8]1[CH:9]=[CH:10][C:5]([NH:1][C:2](=[O:3])[CH3:4])=[CH:6][CH:7]=1)(=[O:13])=[O:12])[CH3:17]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8481N-Acetylsulfanilyl chlorideHCID 77628N,N'-Diisopropylethylenediamine

Product 1

HCID 13983982N-[4-[[(1-Methylethyl)-[2-[(1-methylethyl)amino]ethyl]amino]sulfonyl]phenyl]acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-Acetaminobenzene sulfonyl chloride (23.3 g, 0.1 mole) as a slurry in 400 ml methylene chloride was added to N,N'-diisopropyl ethylene diamine (14.46 g, 0.1 mole) and triethylamine (10.1 g, 0.1 mole) in methylene chloride (600 ml). The reaction was stirred overnight at room temperature. The reaction was washed with water, insoluble by-product filtered off, and the filtrate stripped to a brown gum. After filtration through silica gel in 20% MeOH/EtOAc the crude crystalline product was recrystallized from isopropanol to provide the title product as the hydrochloride salt (3.00 g, m.r. 176°-178° C.).

Workup

  1. washThe reaction was washed with water, insoluble by-product
  2. filtrationfiltered off
  3. filtrationAfter filtration through silica gel in 20% MeOH/EtOAc the crude crystalline product
  4. customwas recrystallized from isopropanol

Sources & evidence

ORD record
ord-038cba76d4d746689662f8c1186f692e
Source dataset
uspto-grants-1987_10
Patent number
US04698445

Reaction notes

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