2-[(5-Dimethylaminomethyl-4-methyl-2-furyl)methylthio]ethylamine → HCID 178427283, compound

HRID 1577507Notes

Reaction equation

HRID 1577507 reaction equation
[NH2:1][CH2:2][CH2:3][S:4][CH2:5][C:6]1[O:10][C:9]([CH2:11][N:12]([CH3:14])[CH3:13])=[C:8]([CH3:15])[CH:7]=1.[N+:16]([NH:19][C:20](=[NH:23])SC)([O-:18])=[O:17]>C(O)C>[CH3:13][N:12]([CH2:11][C:9]1[O:10][C:6]([CH2:5][S:4][CH2:3][CH2:2][NH:1][C:20]([NH:19][N+:16]([O-:18])=[O:17])=[NH:23])=[CH:7][C:8]=1[CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 131251172-[(5-Dimethylaminomethyl-4-methyl-2-furyl)methylthio]ethylamineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 178427283HCID 178427283, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 5-[[2-(amino)ethyl]thio]methyl-N,N,3-trimethyl-2-furanmethanamine (1.14 g) and N-nitro-S-methyl-isothiourea (0.65 g) in ethanol (10 ml) was warmed for 5 minutes and stirred for 30 minutes at ambient temperature. The solvent was removed in vacuo and the residue purified by column chromatography (silica/methanol: 0.88 ammonia 100:1). The resulting oil was triturated with petroleum ether (40°-60°) and the solid residue crystallised from toluene yielding the title compound (0.5 g) as a white powder m.p. 84°-85°.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue purified by column chromatography (silica/methanol: 0.88 ammonia 100:1)
  3. customThe resulting oil was triturated with petroleum ether (40°-60°)
  4. customthe solid residue crystallised from toluene yielding the title compound (0.5 g) as a white powder m.p. 84°-85°

Sources & evidence

ORD record
ord-b3909ad86338408a9908f66aa37769fa
Source dataset
uspto-grants-1981_09
Patent number
US04288443

Reaction notes

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