(4-Nitrophenyl)acetic acid → HCID 3522175, 화합물

HRID 2117634노트

반응식

HRID 2117634 반응식
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].S(Cl)(Cl)=O.[CH3:18][N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1.C(Cl)Cl>C1COCC1.CN(C=O)C>[CH3:18][N:19]1[CH2:24][CH2:23][N:22]([C:11](=[O:13])[CH2:10][C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:21][CH2:20]1

참가 물질

7

반응물 4

HCID 4661(4-Nitrophenyl)acetic acidHCID 6344DichloromethaneHCID 24386Thionyl ChlorideHCID 531671-Methylpiperazine

생성물 1

HCID 3522175HCID 3522175, 화합물

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매HCID 8028Tetrahydrofuran용매

실험 절차

4-Nitrophenylacetic acid (2.00 g, 0.011 mol) was dissolved in anhydrous THF (20 mL) with gradual addition of thionyl chloride (1.03 mL, 0.0143 mol) and a catalytic amount of DMF (2 drops) at room temperature and stirred for 24 h. On completion, the reaction was quenched in situ with N-methylpiperazine (3.85 g, 0.038 mol) added dropwise in a solution of DCM (20 mL) at room temperature and stirred overnight to give a beige suspension. The solvent was removed in vacuo and the residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL). The organic layer was washed twice, dried over sodium sulfate and filtered. Removal of the solvent in vacuo the title compound as an amber oil, which solidified on standing. LCMS:2.5 min; Rt 0.82 (m/z 264, M+H+) 98%

후처리

  1. customto give a beige suspension
  2. customThe solvent was removed in vacuo
  3. customthe residue partitioned between DCM (30 mL) and sodium hydroxide (1N, 30 mL)
  4. washThe organic layer was washed twice
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customRemoval of the solvent in vacuo the title compound as an amber oil, which
  8. custom2.5 min

출처 및 근거

ORD 기록
ord-eb679a379c6d4c13a9db0e8f585e62ad
출처 데이터셋
uspto-grants-2008_10
특허 번호
US07442698B2

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