Formaldehyde → 1-(6-Chloro-3-pyridylmethyl)-2-(1-nitro-2-trimethylsilylmethylthioethylidene)imidazolidine

HRID 1656920Notes

Reaction equation

HRID 1656920 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[CH:14][N+:15]([O-:17])=[O:16])=[CH:4][CH:3]=1.[CH2:18]=O.[SH:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23]>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:13][CH2:12][NH:11][C:10]2=[C:14]([N+:15]([O-:17])=[O:16])[CH2:18][S:20][CH2:21][Si:22]([CH3:25])([CH3:24])[CH3:23])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 140342Methanethiol, trimethylsilyl-HCID 1809572-Chloro-5-{[2-(nitromethylidene)imidazolidin-1-yl]methyl}pyridine

Product 1

HCID 867473281-(6-Chloro-3-pyridylmethyl)-2-(1-nitro-2-trimethylsilylmethylthioethylidene)imidazolidineYield 39.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.5 g of 1-(6-chloro-3-pyridylmethyl)-2-nitromethyleneimidazolidine, 0.18 g of 37% formaldehyde aqueous solution and 0.24 g of mercaptomethyl trimethylsilane were added to 15 ml of ethanol, and were reacted under reflux for 1 hour. After completing the reaction, the reaction liquor was cooled by ice to precipitate a crystal. The crystal thus precipitated was taken out by filtration, and was washed with a cold ethanol to obtain 0.3 g of the aimed product (Compound No. 20) having a melting point of from 162.3° to 164.3° C.

Workup

  1. customwere reacted
  2. temperatureunder reflux for 1 hour
  3. customthe reaction
  4. temperaturethe reaction liquor was cooled by ice
  5. customto precipitate a crystal
  6. customThe crystal thus precipitated
  7. filtrationwas taken out by filtration
  8. washwas washed with a cold ethanol

Sources & evidence

ORD record
ord-2ec39e5ff78f479f9ecbdbee58eab737
Source dataset
uspto-grants-1993_10
Patent number
US05256674

Reaction notes

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