Diisopropylethylamine → (4-Chloro-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amine

HRID 1931198Notes

Reaction equation

HRID 1931198 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[N:5]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)[N:3]=1.C(N(C(C)C)CC)(C)C.[F:30][C:31]([F:43])([F:42])[O:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]=[N:40][NH2:41])=[CH:35][CH:34]=1>O1CCOCC1>[Cl:8][C:6]1[N:7]=[C:2]([NH:41][N:40]=[CH:39][C:36]2[CH:35]=[CH:34][C:33]([O:32][C:31]([F:30])([F:43])[F:42])=[CH:38][CH:37]=2)[N:3]=[C:4]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[C:12]([C:17]([F:20])([F:19])[F:18])[CH:11]=2)[N:5]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57507188(4,6-Dichloro-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)amineHCID 66679788[1-(4-Trifluoromethoxyphenyl)-methylidene]-hydrazine

Product 1

HCID 76550911(4-Chloro-6-{N'-[1-(4-trifluoromethoxyphenyl)-methylidene]-hydrazino}-[1,3,5]triazin-2-yl)-(4-fluoro-3-trifluoromethylphenyl)-amineYield 67%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4,6-Dichloro-N-(3-trifluoromethyl-4-fluorophenyl)-1,3,5-triazine-2-amine (XVII) (2.0 g, 6.2 mmol) was dissolved in dioxane (40 mL). Diisopropylethyl-amine (1.6 mL, 9.32 mmol) was added followed by [4-(trifluoromethoxy)-benzylidene]hydrazine (XX) (1.3 g, 6.2 mmol). The reaction was stirred at room temperature overnight. The solvent was removed under vacuum, and the residue diluted with ethyl ether (25 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated to a yellow powder. This powder was washed with acetonitrile to give {4-chloro-6-[N′-(4-trifluoromethoxy-benzylidene)hydrazino]-1,3,5-triazin-2-yl}-(4-fluoro-3-trifluoromethylphenyl)-amine (XXI) as a white solid; (2.1 g, 67% yield): m.p. 109-111° C.; 1H NMR (CDCl3): δ 8.9, (bs, 1H); 8.5 (bs, 1H); 7.95 (s, 1H); 7.75 (bs, 2H); 7.45 (bs, 1H); 7.24 (m, 4H); ESI/MS 494 (M+H).

Workup

  1. customThe solvent was removed under vacuum
  2. additionthe residue diluted with ethyl ether (25 mL)
  3. washThe organic phase was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to a yellow powder
  7. washThis powder was washed with acetonitrile

Sources & evidence

ORD record
ord-763bbc523248469eb2785a93f1fa26a8
Source dataset
uspto-grants-2012_05
Patent number
US08188273B2

Reaction notes

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