Ethanol → (4-Fluoro-3-trifluoromethylphenyl)-(4-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-amine

HRID 1931202Notes

Reaction equation

HRID 1931202 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][NH2:9])[N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:12]=2)[N:3]=1.[F:22][C:23]([F:34])([F:33])[O:24][C:25]1[CH:32]=[CH:31][CH:30]=[CH:29][C:26]=1C=O.[CH2:35](O)C>>[F:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:4]2[N:5]=[C:6]([NH:8][N:9]=[CH:35][C:30]3[CH:29]=[CH:26][C:25]([O:24][C:23]([F:22])([F:33])[F:34])=[CH:32][CH:31]=3)[N:7]=[CH:2][N:3]=2)=[CH:12][C:13]=1[C:18]([F:21])([F:20])[F:19]

Participants

4

Reactant 3

HCID 702EthanolHCID 27771922-(Trifluoromethoxy)benzaldehydeHCID 57507192(4-Chloro-6-hydrazino-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine

Product 1

HCID 74437663(4-Fluoro-3-trifluoromethylphenyl)-(4-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-amineYield 38%

Procedure

To a solution of (4-Chloro-6-hydrazino-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine (XXIII) (264 mg, 1.38 mmol) in ethanol (8 mL) was added trifluoromethoxybenzaldehyde (200 mg, 0.694 mmol). The mixture was stirred overnight and filtered to give a white precipitate. The mother liquor was concentrated in vacuo and the residue recrystallized from ethyl acetate. The solids were combined and dried in vacuo to afford the titled compound 3 as white solid (123 mg, 38% yield): m.p. 185-186° C.; ESI/MS 461 (M+H), 459(M−H); 1H NMR (CDCl3): δ 8.5 (bs, 1H), 7.95 (s, 1H), 7.80 (m, 2H), 7.65 (m, 1H), 7.2-7.4, m, 6H).

Workup

  1. filtrationfiltered
  2. customto give a white precipitate
  3. concentrationThe mother liquor was concentrated in vacuo
  4. customthe residue recrystallized from ethyl acetate
  5. customdried in vacuo

Sources & evidence

ORD record
ord-e9d951683236460fa7d52711f0955544
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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