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

HRID 128460Notes

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]

Participants

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

temperatureThe mixture is heated
customgiving a clear solution
filtrationThe suspension is filtered hot through diatomaceous earth
temperatureThe filtrate is heated
additionof hot water is added
additionportion of water is added
customthe solid is collected
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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