Dimethylformamide dimethyl acetal → HCID 23469720, compound

HRID 128462Notes

Reaction equation

HRID 128462 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([C:13]3[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=3)=[N:11][CH:10]=[N:9]2)=[CH:4][CH:3]=1.CO[CH:22](OC)[N:23]([CH3:25])[CH3:24]>CN(C)C=O>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:8]([C:5]3[CH:4]=[CH:3][C:2]([N:1]=[CH:22][N:23]([CH3:25])[CH3:24])=[CH:7][CH:6]=3)[N:9]=[CH:10][N:11]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 23469718HCID 23469718, compound

Product 1

HCID 23469720HCID 23469720, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 1.7 g. portion of 1-(p-aminophenyl)-5-(p-fluorophenyl)-1H-1,2,4-triazole is gently refluxed in a mixture of 5.0 ml. of dimethylformamide dimethylacetal and 2.5 ml. of dimethylformamide. Heating is continued for 1.5 hours, then the mixture is evaporated under high vacuum (70° C.) to a brown oil. This oil is triturated with 50 ml. of ether. The solid is collected by filtration, dried and recrystallized from 25 ml. of hot cyclohexane, giving 1.1 g. of the desired product as a light tan solid, mp. 90°-93° C.

Workup

  1. temperatureHeating
  2. customthe mixture is evaporated under high vacuum (70° C.) to a brown oil
  3. customThis oil is triturated with 50 ml
  4. filtrationThe solid is collected by filtration
  5. customdried
  6. customrecrystallized from 25 ml
  7. customof hot cyclohexane, giving 1.1 g

Sources & evidence

ORD record
ord-5ec0f20bb3e84ed28b1a35fed2f590a8
Source dataset
uspto-grants-1981_03
Patent number
US04259504

Reaction notes

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