Diethyl Ether → 5-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

HRID 2406111

反応式

HRID 2406111 の反応式
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH3:9])[C:4]=1[NH:10][NH2:11].C(O[CH:15]=[C:16]([C:19]#[N:20])[C:17]#[N:18])C.C(N(CC)CC)C.C(OCC)C>C(O)C>[NH2:20][C:19]1[N:10]([C:4]2[C:5]([CH3:9])=[CH:6][CH:7]=[CH:8][C:3]=2[CH3:2])[N:11]=[CH:15][C:16]=1[C:17]#[N:18]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 671522-(Ethoxymethylene)propanedinitrileHCID 124050102,6-Dimethylphenylhydrazine hydrochloride

生成物 1

HCID 121505545-Amino-1-(2,6-dimethylphenyl)-1H-pyrazole-4-carbonitrile

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

3.0 g (17.3 mmol) of 2,6-dimethylphenylhydrazine hydrochloride are suspended with 2.1 g (17.3 mmol) of ethoxymethylenemalononitrile in 40 ml of ethanol, and 7.3 ml (52.1 mmol) of triethylamine are added. The reaction mixture is heated to reflux for 3 h, during which a clear solution forms. After cooling to room temperature, diethyl ether is added to this. The triethylammonium chloride which precipitates is filtered off. The solvent is removed in vacuo, and the residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B). 2.3 g (62% of theory) of the product are obtained as yellow crystals.

後処理

  1. additionare added
  2. temperatureThe reaction mixture is heated
  3. temperatureto reflux for 3 h, during which a clear solution forms
  4. customThe triethylammonium chloride which precipitates
  5. filtrationis filtered off
  6. customThe solvent is removed in vacuo
  7. customthe residue is purified by preparative HPLC (YMC gel ODS-AQ S 5/15 μm; eluent A: water, eluent B: acetonitrile; gradient: 0 min 30% B, 5 min 30% B, 50 min 95% B)
  8. custom2.3 g (62% of theory) of the product are obtained as yellow crystals

出典と根拠

ORDレコード
ord-6eee0d69dcc648408a359c26045562e4
出典データセット
uspto-grants-2014_08
特許番号
US08809348B2

関連ノート

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