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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 563849
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HRID 563849 반응식
[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
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참가 물질

4

반응물 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

생성물 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-diamine수율 45.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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

후처리

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

출처 및 근거

ORD 기록
ord-2ad7e840110d4aa899cccbc608672773
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08067588B2

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