Ethanol → N-[2-(3-bromophenyl)-2-hydroxyethyl]-N'-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-2-nitro-1,1-ethenediamine

HRID 236255Notes

Reaction equation

HRID 236255 reaction equation
C(O)C.[CH3:4][N:5]([CH2:7][C:8]1[S:12][C:11]([CH2:13][S:14][CH2:15][CH2:16][NH:17][C:18](SC)=[CH:19][N+:20]([O-:22])=[O:21])=[CH:10][C:9]=1[CH3:25])[CH3:6].[Br:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:36])[CH2:34][NH2:35])[CH:30]=[CH:31][CH:32]=1.C(O)(C)C>C(OCC)C>[Br:26][C:27]1[CH:28]=[C:29]([CH:33]([OH:36])[CH2:34][NH:35][C:18]([NH:17][CH2:16][CH2:15][S:14][CH2:13][C:11]2[S:12][C:8]([CH2:7][N:5]([CH3:4])[CH3:6])=[C:9]([CH3:25])[CH:10]=2)=[CH:19][N+:20]([O-:22])=[O:21])[CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-olHCID 678973201-{2-[[5-(Dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethylamino}-1-methylthio-2-nitroethene

Product 1

HCID 67897170N-[2-(3-bromophenyl)-2-hydroxyethyl]-N'-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-2-nitro-1,1-ethenediamineYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

With 7.5 ml of ethanol were mixed 4.5 g of 1-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethylamino}-1-methylthio-2-nitroethene and 3.5 g of DL-[2-(3-bromophenyl)-2-hydroxyethyl]amine, and the resulting mixture was subjected to reaction at room temperature for 30 hours. Thereto were added 5 ml of isopropanol and 30 ml of diethyl ether, and the mixture thus obtained was stirred, after which the crystals formed were collected by filtration. The crystals were recrystallized from 40 ml of isopropanol to obtain 4.3 g (yield 65%) of N-[2-(3-bromophenyl)-2-hydroxyethyl]-N'-{2-[[5-(dimethylamino)methyl-4-methyl-2-thienyl]methylthio]ethyl}-2-nitro-1,1-ethenediamine having a melting point of 104°-106° C.

Workup

  1. customthe resulting mixture was subjected to reaction at room temperature for 30 hours
  2. customthe mixture thus obtained
  3. customafter which the crystals formed
  4. filtrationwere collected by filtration
  5. customThe crystals were recrystallized from 40 ml of isopropanol

Sources & evidence

ORD record
ord-5e9ed521badf4e26ab7ffa2e08247a02
Source dataset
uspto-grants-1987_02
Patent number
US04643849

Reaction notes

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