Sodium Thiosulfate → HCID 68606931、化合物

HRID 2065735ノート

反応式

HRID 2065735 の反応式
[CH3:1][O:2][C:3](=[O:12])[C:4]1[CH:9]=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[Cl:11].[Br-:13].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.CO>[CH3:1][O:2][C:3](=[O:12])[C:4]1[C:9]([Br:13])=[C:8]([NH2:10])[CH:7]=[CH:6][C:5]=1[Cl:11]

参加物

6

反応物 3

HCID 24477Sodium ThiosulfateHCID 5200412Methyl 5-Amino-2-chlorobenzoateHCID 23500184Tetra-n-butylammonium tribromide

生成物 1

HCID 68606931HCID 68606931、化合物収率 28%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
25 °C

実験手順

To a solution of 5-amino-2-chloro-benzoic acid methyl ester (6.76 g, 36.4 mmol) in dichloromethane (100 mL) and methanol (50 mL) was added tetra-n-butylammonium tribromide (17.7 g, 36.4 mmol). The mixture was stirred at 25° C. for 90 minutes. Sodium thiosulfate (10% aqueous solution) was added and the mixture was extracted with dichloromethane. The combined extracts were washed with water, dried (Na2SO4), filtered, and concentrated to dryness under reduced pressure. The crude material was purified by flash column chromatography (hexane/acetone 8:2). Fractions with the desired product were concentrated to small volume. The resulting suspension was allowed to stand for two hours and was then filtered to obtain 5-amino-6-bromo-2-chloro-benzoic acid methyl ester as a white solid (2.7 g, 28%).

後処理

  1. extractionthe mixture was extracted with dichloromethane
  2. washThe combined extracts were washed with water
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe crude material was purified by flash column chromatography (hexane/acetone 8:2)
  7. concentrationFractions with the desired product were concentrated to small volume
  8. waitto stand for two hours
  9. filtrationwas then filtered

出典と根拠

ORDレコード
ord-019d505be7c3401e86ca3cc3e505a230
出典データセット
uspto-grants-2012_10
特許番号
US08288552B2

反応ノート

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