Propyl isocyanate → 2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one

HRID 2106760Notes

Reaction equation

HRID 2106760 reaction equation
N1([C:7](=[N:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[CH3:8])CCOCC1.[N:20]([CH2:23][CH2:24][CH3:25])=[C:21]=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:8][C:7]1[N:20]([CH2:23][CH2:24][CH3:25])[C:21](=[O:22])[N:10]([C:11]2[CH:12]=[CH:13][C:14]([N+:17]([O-:19])=[O:18])=[CH:15][CH:16]=2)[N:9]=1

Participants

5

Reactant 2

HCID 61033Propyl isocyanateHCID 536875471-(4-Morpholinyl)ethylidene-2-(4-nitrophenyl)hydrazine

Product 1

HCID 151254762,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-oneYield 65%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 13 parts of 1-[1-(4-morpholinyl)ethylidene-2-(4-nitrophenyl)hydrazine, 8.5 parts of 1-isocyanatopropane, 1 part of N,N-dimethyl-4-pyridinamine and 39 parts of dichloromethane was stirred and refluxed for 2 hours. The whole was evaporated and 90 parts of dimethylbenzene were added to the residue. Stirring at reflux was continued for 3 hours. The reaction mixture was cooled and filtered over diatomaceous earth. The filtrate was saturated with petroleum ether. The precipitated product was filtered off and crystallized from 2-propanol, yielding 8.5 parts (65%) of 2,4-dihydro-5-methyl-2-(4-nitrophenyl)-4-propyl-3H-1,2,4-triazol-3-one; mp. 125.4° C. (int. 20).

Workup

  1. temperaturerefluxed for 2 hours
  2. customThe whole was evaporated
  3. addition90 parts of dimethylbenzene were added to the residue
  4. stirringStirring
  5. temperatureat reflux
  6. temperatureThe reaction mixture was cooled
  7. filtrationfiltered over diatomaceous earth
  8. filtrationThe precipitated product was filtered off
  9. customcrystallized from 2-propanol

Sources & evidence

ORD record
ord-c1c36c0d8aac48e5be0cdeab419b407e
Source dataset
uspto-grants-1990_06
Patent number
US04931444

Reaction notes

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