S,N-dimethyl-N'-nitroisothiourea → HCID 137226518, compound

HRID 1647847Notes

Reaction equation

HRID 1647847 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][NH:7][CH2:8][CH3:9])[CH2:2]1.CS[C:12](=[N:17][CH3:18])[NH:13][N+:14]([O-:16])=[O:15]>CN(C1C=CN=CC=1)C.C(O)C>[O:1]1[CH2:5][CH2:4][CH:3]([CH2:6][N:7]([CH2:8][CH3:9])[C:12]([NH:17][CH3:18])=[N:13][N+:14]([O-:16])=[O:15])[CH2:2]1

Participants

5

Reactant 2

HCID 11051832S,N-dimethyl-N'-nitroisothioureaHCID 22355252N-Ethyltetrahydro-3-furanmethanamine

Product 1

HCID 137226518HCID 137226518, compoundYield 23.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 702EthanolSolvent

Procedure

A mixture comprising 5.5 g of N-{(tetrahydro-3-furanyl)methyl}-N-ethylamine, 3.0 g of S-methyl-N-nitro-N'-methyisothiourea, 30 ml of ethanol and 0.5 g of DMAP was refluxed for 4 hours. Then, the reaction fluid was concentrated under a reduced pressure to obtain an oily matter, which was purified by column chromatography. 1.1 g of 1-{(tetrahydro-3-furanyl)methyl}-1-ethyl-2-nitro-3-methylguanidine were obtained.

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationThen, the reaction fluid was concentrated under a reduced pressure
  3. customto obtain an oily matter, which
  4. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e9aa342d44b642a6b7382ce1193c0bbd
Source dataset
uspto-grants-1995_07
Patent number
US05434181

Reaction notes

Loading…