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Acetonitrile → 2-Cyano-4'-[1-(p-fluorophenyl)-1H-1,3,4-triazol-5-yl]acetanilide

HRID 128460
Notes
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Reaction equation

HRID 128460 reaction equation
P(Cl)(Cl)Cl.[NH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)N=C[N:13]=2)=[CH:8][CH:7]=1.[C:24]([CH2:26][C:27]([OH:29])=O)#[N:25].[C:30](#[N:32])C>C(N(CC)CC)C>[C:24]([CH2:26][C:27]([NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH:30]=[N:32][N:13]=2)=[CH:10][CH:11]=1)=[O:29])#[N:25]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 9740Cyanoacetic acidHCID 24387Phosphorus trichlorideHCID 126766705-(p-Aminophenyl)-1-(p-fluorophenyl)-1H-1,2,4-triazole

Product 1

HCID 234697212-Cyano-4'-[1-(p-fluorophenyl)-1H-1,3,4-triazol-5-yl]acetanilide

Reagents, catalysts & solvents 1

HCID 8471
Triethylamine
Solvent

Conditions

Temperature
5 °C

Procedure

A solution of 3.5 ml. of phosphorus trichloride in 25 ml. of acetonitrile is added dropwise to a stirred suspension of 19.0 g. of 5-(p-aminophenyl)-1-(p-fluorophenyl)-1H-1,2,4-triazole in a mixture of 15.6 ml. of triethylamine, 6.35 g. of cyanoacetic acid and 200 ml. of acetonitrile at room temperature over a period of one hour. The mixture is heated to boiling, giving a clear solution and kept at 90° C. for 2.5 hours. The suspension is filtered hot through diatomaceous earth. The filtrate is heated to boiling, 250 ml. of hot water is added and the solution is slowly cooled to 5° C. A 400 ml. portion of water is added and the solid is collected and recrystallized from ethanol giving the desired product as 19.0 g. of cream crystals, mp. 223°-225° C.

Workup

  1. temperatureThe mixture is heated
  2. customgiving a clear solution
  3. filtrationThe suspension is filtered hot through diatomaceous earth
  4. temperatureThe filtrate is heated
  5. additionof hot water is added
  6. additionportion of water is added
  7. customthe solid is collected
  8. customrecrystallized from ethanol giving the desired product as 19.0 g

Sources & evidence

ORD record
ord-db3e86551d084302be386692d5d23beb
Source dataset
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04259504

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes