N-(2-hydroxyethyl)-1,2-dimethylethylenediamine → HCID 178433116, compound

HRID 1492232Notes

Reaction equation

HRID 1492232 reaction equation
CS[C:3](=N)[NH:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[OH:18][CH2:19][CH2:20][NH:21][CH:22]([CH3:26])[CH:23]([CH3:25])[NH2:24]>C(O)C>[CH3:25][CH:23]1[CH:22]([CH3:26])[N:21]([CH2:20][CH2:19][OH:18])[C:3](=[N:4][C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)[NH:24]1

Participants

4

Reactant 2

HCID 18952278N-(2-hydroxyethyl)-1,2-dimethylethylenediamineHCID 178503977HCID 178503977, compound

Product 1

HCID 178433116HCID 178433116, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-methyl-1-(2-morpholinophenyl)-2-thiopseudourea (12.5 g) and N-(2-hydroxyethyl)-1,2-dimethylethylenediamine (8 g) in dry ethanol (150 ml) was heated under reflux at 90°-95° C. for 6 days to give a dark brown oil which was purified by column chromatography on neutral alumina (250 g) using a 1:9 mixture of dichloromethane and hexane to give 4-{2-[4,5-dimethyl-1-(2-hydroxyethyl)-2-imidazolidinylideneamino]phenyl}morpholine as a colourless solid (m.p. 108°-109° C.) which was recrystallised from hexane.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux at 90°-95° C. for 6 days
  3. customto give a dark brown oil which
  4. customwas purified by column chromatography on neutral alumina (250 g)
  5. additiona 1:9 mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-0c96b6b54b5244588b2e1bf18dc0cc91
Source dataset
uspto-grants-1994_12
Patent number
US05373008

Reaction notes

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