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Potassium Carbonate → Ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylate

HRID 1440799
ノート
印刷プレビュー

反応式

HRID 1440799 の反応式
[NH2:1][C:2]1[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[C:33]#[N:34])=[CH:23][CH:22]=1>CN(C)C=O>[C:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[C:24]1[CH:23]=[CH:22][C:21]([CH2:20][NH:1][C:2]2[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:5][N:4]([CH3:12])[N:3]=2)=[CH:26][CH:25]=1)#[N:34]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 252927ethyl 3-amino-1-methyl-1H-pyrazole-4-carboxylateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

生成物 1

HCID 15338339Ethyl 3-[N-(2'-cyanobiphenyl-4-yl)methylamino]-1-methylpyrazole-4-carboxylate収率 76%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a mixture of ethyl 3-amino-1-methylpyrazole-4-carboxylate (P. Schmidt et al. Hel. Chim. Acta., 1959, 41, 349.) (2.30 g) and potassium carbonate in N,N-dimethylformamide (70 ml), was added portionwise 4-bromomethyl-2'-cyanobiphenyl (4.81 g). The solvent was distilled under reduced pressure. To the residue was added ice-water and an aqueous solution of potassium carbonate. The mixture was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, which was dried over magnesium sulfate. The solvent was distilled off under reduced pressure to give crude crystals, which were recrystallization from ethyl acetate-isopropylether to afford the title compound as white crystals (3.7 g, 76%), m.p. 151°-152° C.

後処理

  1. distillationThe solvent was distilled under reduced pressure
  2. additionTo the residue was added ice-water
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materiala saturated aqueous saline solution, which was dried over magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customto give crude crystals, which
  8. customrecrystallization from ethyl acetate-isopropylether

出典と根拠

ORDレコード
ord-9e28ccf1f1c3486092b69c784f0653f5
出典データセット
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05500427

反応ノート

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