Diphenylmethane diisocyanate → Hydrogen Cyanide

HRID 1605538Notes

Reaction equation

HRID 1605538 reaction equation
C1[C:6]([CH2:7][C:8]2C=C[C:11]([N:14]=C=O)=CC=2)=[CH:5][CH:4]=[C:3]([N:17]=C=O)[CH:2]=1>C1(C)C=CC=CC=1>[CH:11]#[N:14].[N:17]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH3:2]

Participants

4

Reactant 1

HCID 7570Diphenylmethane diisocyanate

Product 2

HCID 768Hydrogen CyanideHCID 79372,6-Lutidine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of 21 grams (0.75 mole) of hydrogen cyanide and 85 grams of dry toluene and 10 grams of 2,6-lutidine was prepared at ice bath temperatures. To the solution, 62.5 grams (0.25 mole) of 4,4'-diphenylmethane diisocyanate in 135 grams of dry toluene were added dropwise over a period of two hours. While keeping the temperature below 10° C., a solid began to come out of solution. The reaction solution was stirred an additional 30 minutes after completion of the addition. The product (76 grams) was collected on a filter. The product was purified by dissolving it in acetone and filtering the solution into petroleum ether. The pure product melted at 208° C. Analysis calculated for C17H12N4O2 : C, 67.10; H, 3.97; N, 18.41. Found: C, 66.98; H, 4.22; N, 18.20.

Workup

  1. customthe temperature below 10° C.
  2. additionafter completion of the addition
  3. customThe product (76 grams) was collected on a filter
  4. customThe product was purified
  5. dissolutionby dissolving it in acetone
  6. filtrationfiltering the solution into petroleum ether

Sources & evidence

ORD record
ord-7256d12cdd5f4eb0a5b3d5ce779c683d
Source dataset
uspto-grants-1976_04
Patent number
US03950416

Reaction notes

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