2,4-Difluorobenzene-1-carbothioamide → 3-(2,4-Difluorophenyl)-5-(4-fluoro-3-trifluoromethylphenyl)-[1,2,4]triazine

HRID 1064289Notes

Reaction equation

HRID 1064289 reaction equation
I.[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]([NH:12][NH2:13])=[NH:11].FC1C=C(F)C=CC=1C(N)=S.[F:25][C:26]1[CH:31]=[CH:30][C:29]([C:32](=O)[CH:33]=O)=[CH:28][C:27]=1[C:36]([F:39])([F:38])[F:37]>>[F:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:12]=[N:13][CH:33]=[C:32]([C:29]2[CH:30]=[CH:31][C:26]([F:25])=[C:27]([C:36]([F:39])([F:37])[F:38])[CH:28]=2)[N:11]=1

Participants

4

Reactant 3

HCID 27818682,4-Difluorobenzene-1-carbothioamideHCID 22273600(4-Fluoro-3-trifluoromethylphenyl)oxoacetaldehydeHCID 178506601HCID 178506601, compound2×

Product 1

HCID 104508343-(2,4-Difluorophenyl)-5-(4-fluoro-3-trifluoromethylphenyl)-[1,2,4]triazine

Procedure

2,4-Difluorobenzenecarboximidic hydrazide hydriodide salt was made from 2,4-difluorothiobenzamide using the method described in Example 24. (4-Fluoro-3-trifluoromethylphenyl)oxoacetaldehyde was reacted with 2,4-difluorobenzenecarboximidic hydrazide hydriodide salt using the method described in Example 1 to give 3-(2,4-difluorophenyl)-5-(4-fluoro-3-trifluoromethylphenyl)-[1,2,4]triazine as a yellow solid (795 mg): δH (400 MHz, CDCl3) 7.01-7.13 (2H, m), 7.45 (1H, t, J 9.2 Hz), 8.32-8.38 (1H, m), 8.46-8.50 (1H, m), 8.55 (1H, dd, J 2.3, 6.7 Hz), 9.66 (1H, s); m/z (ES+) 356.

Sources & evidence

ORD record
ord-9b00609af2934876978de19c12018812
Source dataset
uspto-grants-2005_11
Patent number
US06969716B2

Reaction notes

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