1,2-Dichlorobenzene → HCID 178428634, compound

HRID 2372892Notes

Reaction equation

HRID 2372892 reaction equation
C/C(/N)=C\[C:4]#[N:5].Cl[C:8]1C=CC=CC=1Cl.[C:15]([CH2:17][C:18]([NH:20][NH:21][C:22](=O)[CH2:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=O)#[N:16].C([O:35][C:36](=O)[CH3:37])(=O)C>CO>[C:15]([C:17]1[C:36]([OH:35])=[CH:37][C:4]2[N:20]([N:21]=[C:22]([CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[N:5]=2)[C:18]=1[CH3:8])#[N:16]

Participants

6

Reactant 4

HCID 72391,2-DichlorobenzeneHCID 7918Acetic AnhydrideHCID 4190311HCID 4190311, compoundHCID 53247203-Aminocrotonitrile

Product 1

HCID 178428634HCID 178428634, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
100 °C

Procedure

125 g of 3-aminocrotonitrile were introduced into 250 ml of anhydrous o-dichlorobenzene and stirred at 100° C. To this were added 233 g of N-cyanoacetyl-N'-phenoxyacetylhydrazine a little at a time, and the mixture was then stirred at 140° C. for 2 hours. 120 g of acetic anhydride were added and the mixture was then refluxed for 2 hours and, while cooling, 500 ml of methanol were added. After cooling, the precipitate was filtered off with suction, washed with methanol and dried at 80° C. under reduced pressure. 213 g of 6-cyano-7-hydroxy-5-methyl-2-phenoxymethyl[1,2,4]triazolo[2,3-a]-pyridine were obtained as a colorless powder. A sample recrystallized from γ-butyrolactone does not melt up to 350° C. and has the following analysis:

Workup

  1. stirringthe mixture was then stirred at 140° C. for 2 hours
  2. temperaturethe mixture was then refluxed for 2 hours
  3. temperaturewhile cooling
  4. temperatureAfter cooling
  5. filtrationthe precipitate was filtered off with suction
  6. washwashed with methanol
  7. customdried at 80° C. under reduced pressure

Sources & evidence

ORD record
ord-2c7072ca758848b3aa789f3d0b72d9a2
Source dataset
uspto-grants-1992_03
Patent number
US05101028

Reaction notes

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