2-(Trifluoromethyl)phenylhydrazine → 5-n-Butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-one

HRID 1198669

Reaction equation

HRID 1198669 reaction equation
[C:1]([N:6]=[C:7](OCC)[CH2:8][CH2:9][CH2:10][CH3:11])(OCC)=[O:2].[F:15][C:16]([F:26])([F:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[NH:23][NH2:24]>>[CH2:8]([C:7]1[NH:6][C:1](=[O:2])[N:23]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[C:16]([F:25])([F:26])[F:15])[N:24]=1)[CH2:9][CH2:10][CH3:11]

Participants

3

Reactant 2

HCID 5208002-(Trifluoromethyl)phenylhydrazineHCID 53930077ethyl N-carbethoxyvalerimidate

Product 1

HCID 1355270275-n-Butyl-2,4-dihydro-2-[2-(trifluoromethyl)phenyl]-3H-1,2,4-triazol-3-oneYield 66%

Procedure

Ethyl-N-carbethoxyvalerimidate (from Example 3, Step B) was reacted with 2-(trifluoromethyl)phenylhydrazine according to the procedure of Example 3, Step C. Flash chromatography of the crude product on silica gel (gradient elution with 0.5-2% MeOH in CH2Cl2) gave a 66% yield of the title compound as white crystals, mp 124°-126° C.; homogeneous by TLC in 19:1 CH2Cl2 --MeOH; mass spectrum (FAB) m/e 286 (M+1)+.

Sources & evidence

ORD record
ord-9c20c2ce9ae947c9b21655644db5a86d
Source dataset
uspto-grants-1994_01
Patent number
US05281614

Linked notes

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