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

HRID 2406111

반응식

HRID 2406111 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6eee0d69dcc648408a359c26045562e4
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08809348B2

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