(4-Nitrophenyl)acetic acid → HCID 3522175、化合物

HRID 1925386ノート

反応式

HRID 1925386 の反応式
[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

参加物

7

反応物 4

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

生成物 1

HCID 3522175HCID 3522175、化合物

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

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 RT 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 RT 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 sulphate and filtered. Removal of the solvent in vacuo yielded the title compound as an amber oil, 1.50 g (solidified on standing).

後処理

  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 sulphate
  6. filtrationfiltered
  7. customRemoval of the solvent in vacuo

出典と根拠

ORDレコード
ord-2d03554265b34798b9c3450876cd6578
出典データセット
uspto-grants-2012_05
特許番号
US08178557B2

反応ノート

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