Lithium hydroxide, monohydrate → 3-[N-(2,4-Dichloro-benzoyl)-N',N'-dimethyl-hydrazino]-5-phenyl-thiophene-2-carboxylic acid

HRID 73171노트

반응식

HRID 73171 반응식
C[O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]([C:14](=[O:23])[C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=1[Cl:22])[N:11]([CH3:13])[CH3:12])=[O:4].O[Li].O>C1COCC1.CO.O>[Cl:22][C:16]1[CH:17]=[C:18]([Cl:21])[CH:19]=[CH:20][C:15]=1[C:14]([N:10]([C:9]1[CH:8]=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2])[N:11]([CH3:13])[CH3:12])=[O:23]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 597523473-[N-(2,4-Dichloro-benzoyl)-N',N'-dimethyl-hydrazino]-5-phenyl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 100485843-[N-(2,4-Dichloro-benzoyl)-N',N'-dimethyl-hydrazino]-5-phenyl-thiophene-2-carboxylic acid수율 17%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
60 °C

실험 절차

3-[N-(2,4-Dichloro-benzoyl)-N′,N′-dimethyl-hydrazino]-5-phenyl-thiophene-2-carboxylic acid methyl ester (0.050 g, 0.11 mmol) was taken in a mixture of THF:MeOH:H2O (3:2:1, 10 mL) and then added 1N aqueous solution of LiOH.H2O (0.67 mL, 0.67 mmol). The reaction mixture was stirred at 60° C. for 2 h. Solvents were removed and the residue was partitioned between water and ethyl acetate. The aqueous layer was acidified using 10% KHSO4 solution. The organic layer was separated, dried (Na2SO4) and concentrated. The residue was purified by preparative TLC using dicholomethane:methanol (9:1) to obtain 3-[N-(2,4-Dichloro-benzoyl)-N′,N′-dimethyl-hydrazino]-5-phenyl-thiophene-2-carboxylic acid (Compound 72) (0.008 g, 17%). 1H NMR (DMSO, 400 MHz): δ 7.81 (d, 2H), 7.69 (d, 2H), 7.54-7.40 (m, 5H), 2.42 (s, 6H).

후처리

  1. customSolvents were removed
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customThe residue was purified by preparative TLC

출처 및 근거

ORD 기록
ord-ebf3432796e14c9d849b529d4239bfc0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829030B2

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