Hydrochloric Acid → 2-Chloro-1,3-thiazole-4-carboxylic acid

HRID 590919ノート

反応式

HRID 590919 の反応式
N[C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1.[ClH:10].N([O-])=O.[Na+].O>O1CCOCC1.[Cu](Cl)Cl.C(OCC)(=O)C>[Cl:10][C:2]1[S:3][CH:4]=[C:5]([C:7]([OH:9])=[O:8])[N:6]=1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 15018822-Aminothiazole-4-carboxylic acidHCID 23668193Sodium Nitrite

生成物 1

HCID 218030262-Chloro-1,3-thiazole-4-carboxylic acid収率 55%

試薬・触媒・溶媒 3

HCID 24014Cupric Chloride触媒HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
0 °C

実験手順

To a solution of 2.84 g (19.7 mmol) of 2-aminothiazole-4-carboxylic acid in 30 ml of 1,4-dioxane was added 50 ml of concentrated hydrochloric acid, followed by cooling to 0° C., and 10 ml of an aqueous solution of 2.04 g (29.6 mmol) of sodium nitrite was added charged dropwise thereto at 0° C. to 5° C. The reaction liquid was stirred at 0° C. for 2 hours, and then 2.93 g (29.6 mmol) of copper chloride was charged in separate portions thereto. The reaction liquid was returned to room temperature, followed by stirring for 8 hours. To the reaction liquid were added water and ethyl acetate, followed by extraction with ethyl acetate four times. The organic layer was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to prepare 1.77 g (yield 55%) of a target compound.

後処理

  1. additioncharged dropwise
  2. customat 0° C. to 5° C
  3. customThe reaction liquid
  4. customThe reaction liquid
  5. customwas returned to room temperature
  6. stirringby stirring for 8 hours
  7. customTo the reaction liquid
  8. extractionfollowed by extraction with ethyl acetate four times
  9. washThe organic layer was washed with saturated brine
  10. dry with materialdried over anhydrous magnesium sulfate
  11. customThe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-e2ff88eb760a41e29dc6f9fa5d883660
出典データセット
uspto-grants-2016_01
特許番号
US09237745B2

反応ノート

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