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

HRID 1440799
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HRID 1440799 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9e28ccf1f1c3486092b69c784f0653f5
출처 데이터셋
uspto-grants-1996_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05500427

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