Ethylenediamine → 2-(2-Aminoethylamino)-5-nitrophenyl 2-hydroxypropyl sulphone

HRID 978639Notes

Reaction equation

HRID 978639 reaction equation
[OH:1][CH:2]([CH3:17])[CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1Cl)(=[O:6])=[O:5].[CH2:18]([NH2:21])[CH2:19][NH2:20]>C(O)(C)C.O>[OH:1][CH:2]([CH3:17])[CH2:3][S:4]([C:7]1[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:8]=1[NH:20][CH2:19][CH2:18][NH2:21])(=[O:6])=[O:5]

Participants

5

Reactant 2

HCID 3301EthylenediamineHCID 539366392-Chloro-5-nitrophenyl 2-hydroxypropyl sulphone

Product 1

HCID 179937682-(2-Aminoethylamino)-5-nitrophenyl 2-hydroxypropyl sulphone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

28 g (0.1 mol) of 2-chloro-5-nitrophenyl 2-hydroxypropyl sulphone are refluxed in 100 ml of isopropanol. To this are added gradually 15 ml of ethylenediamine, and heating is continued with stirring for a further hour. The cold reaction solution is diluted with 300 ml of water and stirred at 20° C. for two hours. The precipitated yellowish crystals are filtered off with suction, washed with 100 ml of water and dried. This gives 28 g of uniform 2-(2-aminoethylamino)-5-nitrophenyl 2-hydroxypropyl sulphone.

Workup

  1. temperatureheating
  2. stirringstirred at 20° C. for two hours
  3. filtrationThe precipitated yellowish crystals are filtered off with suction
  4. washwashed with 100 ml of water
  5. customdried

Sources & evidence

ORD record
ord-a84b23bf8e94473a9298a238f7dacae9
Source dataset
uspto-grants-1987_05
Patent number
US04665179

Reaction notes

Loading…