p-(Trifluoromethoxy)benzaldehyde → N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamine

HRID 1931196Notes

Reaction equation

HRID 1931196 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[N:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:27])([F:26])[F:25])[CH:18]=3)[N:13]=[C:12]([NH:28][NH2:29])[N:11]=2)=[CH:4][CH:3]=1.[F:30][C:31]([F:42])([F:41])[O:32][C:33]1[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=1>C(O)C>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[N:15]=[C:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[C:19]([C:24]([F:25])([F:27])[F:26])[CH:18]=3)[N:13]=[C:12]([NH:28][N:29]=[CH:37][C:36]3[CH:39]=[CH:40][C:33]([O:32][C:31]([F:30])([F:41])[F:42])=[CH:34][CH:35]=3)[N:11]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 57507190N-(6-Chloro-pyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethylphenyl)-6-hydrazino-[1,3,5]triazine-2,4-diamine

Product 1

HCID 74437664N-(6-Chloropyridin-3-ylmethyl)-N'-(4-fluoro-3-trifluoromethyl-phenyl)-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazine-2,4-diamineYield 45.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 20 mL flask was charged with N-(6-chloropyridin-3-yl-methyl)-N′-(4-fluoro-3-trifluoromethylphenyl)-6-hydrazino-1,3,5-triazine-2,4-diamine (XIX) (285 mg, 0.66 mmol), 4-(trifluoromethoxy)benzaldehyde (251 mg, 1.32 mmol), and ethanol (10 mL), and the resulting mixture stirred at ambient temperature for 24 h. The mixture was concentrated under vacuum, the residue washed with hexanes and recrystallized from hexanes-ethyl ether to afford the titled compound (2) as a white solid (182 mg, 45% yield): m.p. 117-125° C.; 1H NMR (CDCl3): δ 8.65 (bs, 1H); 8.54 (d, J=4.5 Hz, 1H); 8.35 (bs, 1H); 7.84 (s, 1H); 7.73 (d, J=7.2 Hz, 2H); 7.49-7.7 (m, 4H); 7.26 (m, 3H); 7.2 (t, J=6.0 Hz, 1H); 4.66 (d, J=6.0 Hz, 2H); Anal. Calcd for C24H17F7N8O: C, 50.89, H, 3.03, N, 19.78. Found C, 50.49; H, 3.17; N, 19.31

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. washthe residue washed with hexanes
  3. customrecrystallized from hexanes-ethyl ether

Sources & evidence

ORD record
ord-6221536bd83b4c2382709011ff6dc2ca
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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