Sodium hydride → Ethyl 5-(2'-cyanobiphenyl-4-yl)methylamino-1-methylpyrazole-4-carboxylate

HRID 1440800ノート

反応式

HRID 1440800 の反応式
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[H-].[Na+].Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[C:29]#[N:30])=[CH:19][CH:18]=1.[Cl-].[NH4+]>O1CCCC1>[C:29]([C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[C:20]1[CH:19]=[CH:18][C:17]([CH2:16][NH:1][C:2]2[N:6]([CH3:7])[N:5]=[CH:4][C:3]=2[C:8]([O:10][CH2:11][CH3:12])=[O:9])=[CH:22][CH:21]=1)#[N:30]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 271299Ethyl 5-amino-1-methyl-1H-pyrazole-4-carboxylateHCID 15019124'-(Bromomethyl)-2-cyanobiphenyl

生成物 1

HCID 18982083Ethyl 5-(2'-cyanobiphenyl-4-yl)methylamino-1-methylpyrazole-4-carboxylate収率 69%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of ethyl 5-amino-1-methylpyrazole-4-carboxylate (1.6 9 g) (P. Schmidt et al. Helv. Chim. Acta., 1959, 42, 349) in tetrahydrofuran (30 ml) was added at 0° C. sodium hydride (about 60% in oil, 0.48 g). The mixture was stirred for one hour at room temperature. To the reaction mixture was added portionwise at 0° C. 4-bromomethyl-2'-cyanobiphenyl (3.27 g). The mixture was stirred overnight at room temperature. The reaction mixture was poured into a saturated aqueous solution of ammonium chloride, which was extracted with ethyl acetate. The extract was washed with water and a saturated aqueous saline solution, followed by drying over magnesium sulfate. The solvent was distilled under reduced pressure to give crude crystals. Recrystallization from ethyl acetate-isopropyl ether afforded the title compound as colorless crystals (2.47 g, 69%), m.p. 107°-108° C.

後処理

  1. additionTo the reaction mixture was added portionwise at 0° C
  2. stirringThe mixture was stirred overnight at room temperature
  3. extractionwas extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialby drying over magnesium sulfate
  6. distillationThe solvent was distilled under reduced pressure
  7. customto give crude crystals
  8. customRecrystallization from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-0e3aa359b0994c2fbcb4e4c71e514d7c
出典データセット
uspto-grants-1996_03
特許番号
US05500427

反応ノート

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