Ethanol → HCID 136133141, compound

HRID 977109Notes

Reaction equation

HRID 977109 reaction equation
CS[C:3](=[NH:8])[NH:4][N+:5]([O-:7])=[O:6].CN([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1)C.C(O)C.[C:21]([O:24][CH2:25]C)(=O)C>>[O:24]1[CH2:25][CH2:16][CH:15]([CH2:14][N:13]2[CH2:12][CH2:17][NH:8][C:3]2=[N:4][N+:5]([O-:7])=[O:6])[CH2:21]1

Participants

5

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 218852-DimethylaminopyridineHCID 135927615N-Nitro-S-methylisothiourea

Product 1

HCID 136133141HCID 136133141, compound

Procedure

The thus obtained crude oily substance was mixed with 3.07 g of S-methyl-N-nitroisothiourea, 0.1 g of dimethylaminopyridine (DMAP) and 30 ml of ethanol, and the mixture was refluxed. After the completion of reaction, ethyl acetate was added, and insolubles were then removed by filtration. The filtrate was concentrated under a reduced pressure to precipitate crystals, and the thus precipitated crystals were then removed by filtration. Next, the filtrate was concentrated under a reduced pressure to obtain an oily substance, and this oily substance was then purified by silica gel column chromatography (1:2 acetone/ethyl acetate) to obtain 1.04 g of 1-[(tetrahydro-3-furanyl)methyl]-2-(nitroimino)imidazolidine as a pale yellow oil.

Workup

  1. customThe thus obtained crude oily substance
  2. temperaturethe mixture was refluxed
  3. additionwas added
  4. custominsolubles were then removed by filtration
  5. concentrationThe filtrate was concentrated under a reduced pressure
  6. customto precipitate crystals
  7. customthe thus precipitated crystals were then removed by filtration
  8. concentrationNext, the filtrate was concentrated under a reduced pressure
  9. customto obtain an oily substance
  10. customthis oily substance was then purified by silica gel column chromatography (1:2 acetone/ethyl acetate)

Sources & evidence

ORD record
ord-7eb93f9bb7d946b3aedc86a61ab64582
Source dataset
uspto-grants-1997_03
Patent number
US05614527

Reaction notes

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