Lithium Hydroxide → 3-[(2,4-dichlorophenyl)methylamino]-5-phenyl-thiophene-2-carboxylic Acid

HRID 2193905

반응식

HRID 2193905 반응식
C[O:2][C:3]([C:5]1[S:6][C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][C:9]=1[NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[Cl:19])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[Cl:19][C:13]1[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=1[CH2:11][NH:10][C:9]1[CH:8]=[C:7]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[S:6][C:5]=1[C:3]([OH:4])=[O:2]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 207757543-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester

생성물 1

HCID 101101733-[(2,4-dichlorophenyl)methylamino]-5-phenyl-thiophene-2-carboxylic Acid수율 63.2%

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
100 °C

실험 절차

3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid methyl ester (70 mg, 0.18 mmol) was dissolved in a mixture of THF-MeOH—H2O (3:2:1) (20 mL) and then 1080 ul of LiOH 1N was added to it. After 16 h of stirring at temperature of 100° C., solvents were removed and then partitioned between 10 ml of H2O, 2 ml of KHSO4 5% and 10 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (MgSO4) and concentrated to obtain 43 mg (63%) of 3-(2,4-Dichloro-benzylamino)-5-phenyl-thiophene-2-carboxylic acid 1H-NMR (DMSO, 400 MHz): δ 7.65 ppm (m, 3H, Haro); 7.43-7.32 ppm (m, 5H, Haro); 7.23 ppm (s, 1H, Haro); 4.61 ppm (d, 2H, N—CH2).

후처리

  1. customwere removed
  2. custompartitioned between 10 ml of H2O, 2 ml of KHSO4 5% and 10 ml of EtOAc
  3. customThe organic layer was separated
  4. washthe aqueous phase was washed twice with ethyl acetate (2×10 mL)
  5. dry with materialThe combined ethyl acetate layer was dried (MgSO4)
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-41a610c813f44ffd9cc4bcc4afd4f258
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08329924B2

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