Ethyl Acetate → 4-Acetamido-N-(2-amino-5-(thiazol-2-yl)phenyl)benzamide

HRID 252843

反応式

HRID 252843 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[C:6]1[CH:7]=[C:8]([NH2:13])[C:9]([NH2:12])=[CH:10][CH:11]=1.[C:14]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](Cl)=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15].CCOC(C)=O>C(#N)C.N1C=CC=CC=1>[C:14]([NH:17][C:18]1[CH:26]=[CH:25][C:21]([C:22]([NH:13][C:8]2[CH:7]=[C:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH:11]=[CH:10][C:9]=2[NH2:12])=[O:23])=[CH:20][CH:19]=1)(=[O:16])[CH3:15]

参加物

6

反応物 3

HCID 8857Ethyl AcetateHCID 70103414-Acetamidobenzoyl chlorideHCID 130078124-(Thiazol-2-yl)benzene-1,2-diamine

生成物 1

HCID 597366844-Acetamido-N-(2-amino-5-(thiazol-2-yl)phenyl)benzamide収率 5.7%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6342Acetonitrile溶媒2 回

実験手順

To a stirred suspension of 222a (47 mg, 0.25 mmol) in acetonitrile (10 mL) and pyridine (20 uL) was added 4-acetamidobenzoyl chloride (49 mg, 0.25 mmol) in acetonitrile (1 mL) at 0° C. for 15 min. The reaction mixture was warmed up to room temperature and stirred for 4 hours, concentrated under reduced pressure. The crude was diluted in DCM and washed with NaHCO3 and brine. The organic layer was dried with Na2SO4 and evaporated. The residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3), then EtOAc (100%) to afford the title compounds 223 (3 mg, 4% yield) and 224a (5 mg, 5% yield).

後処理

  1. concentrationconcentrated under reduced pressure
  2. additionThe crude was diluted in DCM
  3. washwashed with NaHCO3 and brine
  4. dry with materialThe organic layer was dried with Na2SO4
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel, eluents hexane-EtOAc (1:3)

出典と根拠

ORDレコード
ord-40fc5002ce4e4f40b706f1dcde50eab1
出典データセット
uspto-grants-2011_01
特許番号
US07868205B2

関連ノート

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