2,2-Diethoxyethylamine → HCID 10730704, compound

HRID 1762035Notes

Reaction equation

HRID 1762035 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[N:7]=[C:8]=[S:9].[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][NH2:15])[CH3:11]>C(O)C>[CH2:10]([O:12][CH:13]([O:16][CH2:17][CH3:18])[CH2:14][NH:15][C:8]([NH:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[S:9])[CH3:11]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 992362-Pyridyl isothiocyanate

Product 1

HCID 10730704HCID 10730704, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 11.1 g of 2-pyridylisothiocyanate dissolved in 100 ml of ethanol, was added 10.0 g of aminoacetaldehyde diethylacetal, followed by stirring of the resulting mixture under reflux with heating for 40 minutes. After completion of the reaction, the solvent was distilled off under reduced pressure. Crystals precipitated were collected by filtration to give 13.8 g of N-2,2-diethoxyethyl-N'-(2-pyridyl)thiourea (m.p.: 132° to 133° C.). To the thus obtained crystals was added 120 ml of 10% diluted hydrochloric acid, followed by stirring of the resulting mixture under reflux with heating for 30 minutes. The reaction mixture was cooled and adjusted to pH of 5 to 6 with use of 50% aqueous sodium hydroxide to precipitate crystals. The crystals precipitated were filtered out, washed with water and dried to give 8.3 g of the desired compound. m.p.: 162° to 163° C.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 40 minutes
  3. customAfter completion of the reaction
  4. distillationthe solvent was distilled off under reduced pressure
  5. customCrystals precipitated
  6. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-50dd8deb92a648f38deb23d3fd923a69
Source dataset
uspto-grants-1989_05
Patent number
US04830660

Reaction notes

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