3,4,5,6-Tetrahydrophthalic anhydride → 1-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclobutanecarboxylic acid methyl ester

HRID 1646456ノート

反応式

HRID 1646456 の反応式
[CH3:1][O:2][C:3]([C:5]1([S:9][C:10]2[CH:15]=[C:14]([NH2:16])[C:13]([F:17])=[CH:12][C:11]=2[Cl:18])[CH2:8][CH2:7][CH2:6]1)=[O:4].[C:19]1(=O)[O:24][C:22](=[O:23])[C:21]2[CH2:25][CH2:26][CH2:27][CH2:28][C:20]1=2>C(O)(=O)C>[CH3:1][O:2][C:3]([C:5]1([S:9][C:10]2[CH:15]=[C:14]([N:16]3[C:22](=[O:23])[CH:21]4[C:20](=[CH:28][CH2:27][CH2:26][CH2:25]4)[C:19]3=[O:24])[C:13]([F:17])=[CH:12][C:11]=2[Cl:18])[CH2:8][CH2:7][CH2:6]1)=[O:4]

参加物

4

反応物 2

HCID 124753,4,5,6-Tetrahydrophthalic anhydrideHCID 544812611-(5-Amino-2-chloro-4-fluorophenylthio)-cyclobutanecarboxylic acid methyl ester

生成物 1

HCID 678545351-[2-Chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclobutanecarboxylic acid methyl ester収率 62.1%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 4.4 g of 1-(5-amino-2-chloro-4-fluorophenylthio)-cyclobutanecarboxylic acid methyl ester and 2.4 g of 3,4,5,6-tetrahydrophthalic anhydride in 60 ml of glacial acetic acid is heated under reflux for 5 hours while stirring. The reaction mixture is then introduced into ice-water and the resulting glutinous product is extracted with ethyl acetate. After drying the organic phase over sodium sulfate and concentrating by evaporation in vacuo, petroleum ether is added to the resulting residue and the substance solidifies. Filtering yields 4 g of 1-[2-chloro-4-fluoro-5-(1,2,3,4,5,6-hexahydro-1,3-dioxo-isoindolyl)-phenylthio]-cyclobutanecarboxylic acid methyl ester having a melting point of +98° C.

後処理

  1. temperatureis heated
  2. temperatureunder reflux for 5 hours
  3. extractionthe resulting glutinous product is extracted with ethyl acetate
  4. dry with materialAfter drying the organic phase over sodium sulfate
  5. concentrationconcentrating by evaporation in vacuo, petroleum ether
  6. additionis added to the resulting residue
  7. filtrationFiltering

出典と根拠

ORDレコード
ord-be138bb298df4b7d80d5d89b37dc8675
出典データセット
uspto-grants-1993_01
特許番号
US05180418

反応ノート

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