Benzaldehyde → HCID 89649860、化合物

HRID 531193ノート

反応式

HRID 531193 の反応式
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:9](#[N:13])[CH2:10][C:11]#[N:12].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH2:33][C:32](=[O:34])[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]=2)=[CH:25][CH:24]=1>C(O)C>[NH2:12][C:11]1[O:34][C:32]2[N:31]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[N:30]=[C:29]([C:26]3[CH:25]=[CH:24][C:23]([O:22][CH3:21])=[CH:28][CH:27]=3)[C:33]=2[CH:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]=1[C:9]#[N:13]

参加物

6

反応物 4

HCID 240BenzaldehydeHCID 8010MalononitrileHCID 8471TriethylamineHCID 103081595-(4-Methoxyphenyl)-2-phenyl-2,4-dihydro-3H-pyrazol-3-one

生成物 1

HCID 89649860HCID 89649860、化合物収率 58%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of benzaldehyde (290 μL, 2.87 mmol, 1.0 equ.), malononitrile (190 mg, 2.87 mmol, 1.0 equ.) and triethylamine (400 μL, 2.87 mmol, 1.0 equ.) in ethanol (10 mL) was stirred for 1 min, followed by the addition of 3-(4-methoxyphenyl)-1-phenyl-1H-pyrazol-5(4H)-one (764 mg, 2.87 mmol, 1 equ.). The reaction mixture was concentrated after 19 h and washed with ethanol and hexanes, re-crystallized from ethanol, and washed with hexanes and ethanol to give 6-amino-3-(4-methoxyphenyl)-1,4-diphenyl-1,4-dihydropyrano[2,3-c]pyrazole-5-carbonitrile (695 mg, 1.65 mmol, 58%) as a white solid. 1H-NMR (400 MHz) DMSO: 7.94-7.92 (d, 2H), 7.58-7.53 (m, 2H), 7.41-7.37 (t, 1H), 7.27-7.16 (m, 7H), 6.83-6.81 (d, 2H), 5.04 (s, 1H), 3.71 (s, 3H), 13C-NMR (100 MHz) DMSO: 159.5, 159.0, 146.6, 145.6, 144.5, 137.9, 129.8, 128.9, 128.3, 128.0, 127.3, 127.1, 125.1, 121.1, 120.3, 114.1, 97.5, 59.8, 55.5, 37.9; LC/MS-MS: 421.2→355.0 m/z; GS1 and GS2 at 30, DP=71, CE=33, CXP=24, tR=4.28 min.

後処理

  1. concentrationThe reaction mixture was concentrated after 19 h
  2. washwashed with ethanol and hexanes
  3. customre-crystallized from ethanol
  4. washwashed with hexanes and ethanol

出典と根拠

ORDレコード
ord-1ca565cfb68b4fd08243243a0ad2b3f7
出典データセット
uspto-grants-2016_05
特許番号
US09353121B2

反応ノート

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