Cyanoacetic acid → 2-cyano-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide

HRID 59860Notes

Reaction equation

HRID 59860 reaction equation
[C:1]([CH2:3][C:4]([OH:6])=O)#[N:2].[F:7][C:8]([F:29])([F:28])[O:9][C:10]1[CH:15]=[CH:14][C:13]([N:16]2[CH:20]=[N:19][C:18]([C:21]3[CH:27]=[CH:26][C:24]([NH2:25])=[CH:23][CH:22]=3)=[N:17]2)=[CH:12][CH:11]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]([CH2:3][C:4]([NH:25][C:24]1[CH:26]=[CH:27][C:21]([C:18]2[N:19]=[CH:20][N:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][C:8]([F:7])([F:29])[F:28])=[CH:11][CH:12]=3)[N:17]=2)=[CH:22][CH:23]=1)=[O:6])#[N:2]

Participants

5

Reactant 3

HCID 9740Cyanoacetic acidHCID 10868DicyclohexylcarbodiimideHCID 578244904-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline

Product 1

HCID 712093072-cyano-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamideYield 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cyanoacetic acid (0.30 g, 3.53 mmol) and 4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)aniline (1.00 g, 3.12 mmol) were dissolved in 30 mL of dichloromethane, and then dicyclohexylcarbodiimide (0.695 g, 3.37 mmol) was added in one portion as a solid. The solution was allowed to stir for 2 h, then the solvent was removed and the residue was heated in 75 mL of EtOAc, cooled and filtered to remove dicyclohexyl urea. The filtrate was concentrated and the solid was recrystallized from EtOH to give 0.82 g (66%) of 2-cyano-N-(4-(1-(4-(trifluoromethoxy)phenyl)-1H-1,2,4-triazol-3-yl)phenyl)acetamide (B11) as a white solid, mp 250-252° C. 1H NMR (DMSO-d6) δ 10.51 (s, 1H), 9.39 (s, 1H), 8.13-8.00 (m, 4H), 7.75-7.66 (m, 2H), 7.62 (d, J=8.3 Hz, 2H), 3.95 (s, 2H). ESIMS m/z 388 (M+H).

Workup

  1. customthe solvent was removed
  2. temperaturethe residue was heated in 75 mL of EtOAc
  3. temperaturecooled
  4. filtrationfiltered
  5. customto remove dicyclohexyl urea
  6. concentrationThe filtrate was concentrated
  7. customthe solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-97200031b9994480968a65af67da2e1c
Source dataset
uspto-grants-2016_09
Patent number
US09440964B2

Reaction notes

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