1,3-Propanediamine → N,N"-1,3-Propanediylbis-[N'-[3-[3-[(dimethylamino) methyl]phenoxy]propyl]thiourea]

HRID 1902847Notes

Reaction equation

HRID 1902847 reaction equation
[N:1]([CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[C:10]([CH2:14][N:15]([CH3:17])[CH3:16])[CH:11]=[CH:12][CH:13]=1)=[C:2]=[S:3].[NH2:18][CH2:19][CH2:20][CH2:21][NH2:22]>C(#N)C>[CH2:21]([NH:22][C:2]([NH:1][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:16])[CH3:17])[CH:9]=1)=[S:3])[CH2:20][CH2:19][NH:18][C:2]([NH:1][CH2:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][N:15]([CH3:16])[CH3:17])[CH:9]=1)=[S:3]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 20513976HCID 20513976, compound

Product 1

HCID 20549772N,N"-1,3-Propanediylbis-[N'-[3-[3-[(dimethylamino) methyl]phenoxy]propyl]thiourea]Yield 17.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-(3-isothiocyanatopropoxy)-N,N-dimethylbenzenemethanamine (2.24 g) and 1,3-diaminopropane (0.42 g) in acetonitrile (50 ml) was stirred at room temperature for 24 hours. The solvent was evaporated in vacuo and the oily residue chromatographed (silica/methanol) to yield the title compound (0.46 g) as a gum.

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe oily residue chromatographed (silica/methanol)

Sources & evidence

ORD record
ord-5737217953364548aa269a844b9e81de
Source dataset
uspto-grants-1982_12
Patent number
US04366164

Reaction notes

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