Methyl Isocyanate → Benzaldehyde (2-cyanoethyl)(N-methylcarbamoyl)hydrazone

HRID 2394489Notes

Reaction equation

HRID 2394489 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[C:5]([CH2:7][CH2:8][NH:9][N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:6]>C1C=CC=CC=1>[C:5]([CH2:7][CH2:8][N:9]([C:3](=[O:4])[NH:2][CH3:1])[N:10]=[CH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)#[N:6]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 85132177Benzaldehyde (2-cyanoethyl)hydrazone

Product 1

HCID 53679320Benzaldehyde (2-cyanoethyl)(N-methylcarbamoyl)hydrazone

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

0.57 g (10-2 moles) of methyl isocyanate is added, at 25° C., to a solution of 10-2 moles of benzaldehyde (2-cyanoethyl)hydrazone in 30 ml of anhydrous benzene. The mixture is then heated to boiling temperature and left under reflux for 30 minutes. On cooling, the acylated compound crystallizes. It is filtered, drained and then recrystallized from a mixture of benzene and cyclohexane. Its melting point is 145° C. The reaction yield is 48%.

Workup

  1. temperatureThe mixture is then heated
  2. waitleft
  3. temperatureunder reflux for 30 minutes
  4. temperatureOn cooling
  5. customthe acylated compound crystallizes
  6. filtrationIt is filtered
  7. customrecrystallized from a mixture of benzene and cyclohexane
  8. customThe reaction yield is 48%

Sources & evidence

ORD record
ord-7643e30546bf4b9cb1a9e06f4862edd9
Source dataset
uspto-grants-1998_09
Patent number
US05811456

Reaction notes

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