N,N-Diethylethylenediamine → 4-(6-Chloro-4-quinazolinylamino)-N-(2-diethylaminoethyl)benzenesulphonamide

HRID 1383074Notes

Reaction equation

HRID 1383074 reaction equation
Cl.S(Cl)(Cl)(=O)=O.[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([S:25]([OH:28])(=[O:27])=O)=[CH:21][CH:20]=1.[CH2:29]([N:31]([CH2:35][CH3:36])[CH2:32][CH2:33][NH2:34])[CH3:30]>>[Cl:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[CH:13][N:12]=[C:11]2[NH:18][C:19]1[CH:20]=[CH:21][C:22]([S:25]([NH:34][CH2:33][CH2:32][N:31]([CH2:35][CH3:36])[CH2:29][CH3:30])(=[O:27])=[O:28])=[CH:23][CH:24]=1

Participants

4

Reactant 3

HCID 60993N,N-DiethylethylenediamineHCID 135372094-(6-Chloro-4-quinazolinylamino)benzenesulphonic acidHCID 19012189Sulphonylchloride hydrochloride

Product 1

HCID 135372104-(6-Chloro-4-quinazolinylamino)-N-(2-diethylaminoethyl)benzenesulphonamide

Procedure

The sulphonyl chloride hydrochloride derivative of the sulphonic acid or part (a) was used to sulphonylate N,N-diethylethylenediamine using a similar procedure to Example 8. The crude product obtained after evaporation of solvent from the chloroform layer was a brown solid which was purified by column chromatography (basic alumina: 1% ethanol/chloroform) to give a creamy white solid. Recrystallisation from ethanol/water gave the title compound hemihydrate, m.p. 110°-113° C. Analysis: Calculated for C20H24ClNSO2S.1/2H2O C, 54.2%; H, 5.69%; N, 15.8%. Found C, 54.3%; H, 5.64%; N, 16.1%.

Workup

  1. customThe crude product obtained
  2. customafter evaporation of solvent from the chloroform layer
  3. customwas purified by column chromatography (basic alumina: 1% ethanol/chloroform)
  4. customto give a creamy white solid
  5. customRecrystallisation from ethanol/water

Sources & evidence

ORD record
ord-dde01f6918cb40a986e690b44be734ec
Source dataset
uspto-grants-1989_02
Patent number
US04808715

Reaction notes

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