Water → HCID 15391109, compound

HRID 1280433Notes

Reaction equation

HRID 1280433 reaction equation
C[O-].[Na+].Cl.Cl.[CH2:6]([NH:13][NH2:14])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[C:15]([CH2:17][C:18]([C:20]1[O:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=1)=O)#[N:16].O>C(O)C>[NH2:16][C:15]1[N:13]([CH2:6][C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:14]=[C:18]([C:20]2[O:21][C:22]([CH2:25][OH:26])=[CH:23][CH:24]=2)[CH:17]=1

Participants

6

Reactant 4

HCID 962WaterHCID 146540Benzylhydrazine dihydrochlorideHCID 10942334Sodium MethoxideHCID 15391114HCID 15391114, compound

Product 1

HCID 15391109HCID 15391109, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

44.1 g (817 mmol) of sodium methoxide is added with stirring to a solution of 79.5 g (408 mmol) of benzylhydrazine dihydrochloride in 1.3 l of ethanol. After 15 min 67.4 g (408 mmol) of 2-cyanomethylcarbonyl-5-hydroxymethylfuran are added and the mixture is stirred under reflux for 3 hours. After cooling, 1 l of water is added, the ethanol part is evaporated in vacuo and the precipitated crystals are filtered off with suction. After washing, with water and then with ether, the precipitate is dried over P2O5, 91 g(83% of theory) of product having an m.p. of 163° C. are obtained.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. customthe ethanol part is evaporated in vacuo
  4. filtrationthe precipitated crystals are filtered off with suction
  5. washAfter washing, with water
  6. dry with materialwith ether, the precipitate is dried over P2O5, 91 g(83% of theory) of product
  7. customare obtained

Sources & evidence

ORD record
ord-3850154c018c4a86b52d6184e90244c9
Source dataset
uspto-grants-2002_09
Patent number
US06451805B1

Reaction notes

Loading…