Acetamidine monohydrochloride → HCID 12877072, compound

HRID 1154739Notes

Reaction equation

HRID 1154739 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11]([NH:13][NH2:14])=[O:12])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl.[C:16](=N)(N)[CH3:17].C([O-])(=O)C.[Na+]>O>[CH3:16][C:17]1[N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[C:11](=[O:12])[NH:13][N:14]=1

Participants

5

Reactant 3

HCID 67170Acetamidine monohydrochlorideHCID 517045Sodium AcetateHCID 12467017N-(4-Nitrophenyl)hydrazinecarboxamide

Product 1

HCID 12877072HCID 12877072, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 4 parts of N-(4-nitrophenyl)hydrazinecarboxamide, 5 parts of ethanimidamide hydrochloride and 5 parts of sodium acetate is stirred and heated for 4 hours at 140° C. The reaction mixture is cooled, water is added and the whole is stirred till the product is crystallized. It is filtered off and recrystallized from 2-propanol, yielding 1.5 parts (34%) of 2,4-dihydro-5-methyl-4-(4-nitrophenyl)-3H-1,2,4-triazol-3-one; mp. 226.1° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. stirringthe whole is stirred till the product
  3. customis crystallized
  4. filtrationIt is filtered off
  5. customrecrystallized from 2-propanol

Sources & evidence

ORD record
ord-be5d8930e64d44729da46eddf76f6cf5
Source dataset
uspto-grants-1984_12
Patent number
US04490530

Reaction notes

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