Chloroform → Ethyl 2-chloro-5-phenylthiazole-4-carboxylate

HRID 383909

反応式

HRID 383909 の反応式
N[C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1.[N+]([O-])(OCCC(C)C)=O.C(Cl)(Cl)[Cl:28].[OH-].[Na+]>CC#N>[Cl:28][C:2]1[S:3][C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:5]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[N:6]=1

参加物

6

反応物 4

HCID 6212ChloroformHCID 10985Isoamyl nitrateHCID 14798Sodium HydroxideHCID 12603728Ethyl 2-amino-5-phenyl-1,3-thiazole-4-carboxylate

生成物 1

HCID 59291332Ethyl 2-chloro-5-phenylthiazole-4-carboxylate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

To a solution of ethyl 2-amino-5-phenylthiazole-4-carboxylate in MeCN was added CuCl2 at 0° C., and the isoamyl nitrate was slowly added dropwise thereto, followed by stirring for 1 hour. To the reaction mixture was added CHCl3, followed by stirring at 0° C. for 2 hours and then at room temperature for 2 hours. The reaction mixture was neutralized by addition of a 1 M aqueous NaOH solution, and filtered through Celite. The filtrate was extracted with EtOAc, and the organic layer was washed with water and brine in this order and then dried over MgSO4. After concentration under reduced pressure, the residue obtained was purified by medium-pressure preparative liquid chromatography (silica gel YAMAZEN YFLC WPrep2XY, hexane:EtOAc) to obtain ethyl 2-chloro-5-phenylthiazole-4-carboxylate as a yellow oil.

後処理

  1. stirringby stirring at 0° C. for 2 hours
  2. waitat room temperature for 2 hours
  3. filtrationfiltered through Celite
  4. extractionThe filtrate was extracted with EtOAc
  5. washthe organic layer was washed with water and brine in this order
  6. dry with materialdried over MgSO4
  7. concentrationAfter concentration under reduced pressure
  8. customthe residue obtained
  9. customwas purified by medium-pressure preparative liquid chromatography (silica gel YAMAZEN YFLC WPrep2XY, hexane:EtOAc)

出典と根拠

ORDレコード
ord-0c053e4a2d1c430b8f52df4f7ffa7ef9
出典データセット
uspto-grants-2013_02
特許番号
US08367696B2

関連ノート

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