Acetic Acid → 2-Chloro-5-phenyl-1,3-thiazole

HRID 420547

反応式

HRID 420547 の反応式
N[C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1.[ClH:13].C(O)(=O)C.N([O-])=O.[Na+]>O.O.[Cu](Cl)Cl.C(Cl)(Cl)Cl.O>[Cl:13][C:2]1[S:3][C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:5][N:6]=1

参加物

8

反応物 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 8731195-Phenyl-thiazol-2-ylamineHCID 23668193Sodium Nitrite

生成物 1

HCID 217888402-Chloro-5-phenyl-1,3-thiazole

試薬・触媒・溶媒 3

HCID 61482Cupric chloride dihydrate触媒HCID 962Water溶媒HCID 6212Chloroform溶媒

反応条件

温度
40 °C

実験手順

To a mixture of 2-amino-5-phenylthiazole described in Journal of Medicinal Chemistry, 1983, Vol. 26 (8), 1158-1163, (1.00 g; 5.67 mmol), copper (II) chloride dihydrate (1.94 g; 11.3 mmol), concentrated hydrochloric acid (8 ml) and acetic acid (8 ml) was added sodium nitrite (0.47 g; 6.80 mmol) under ice-cooling. The mixture was stirred at 40° C. for 1 hour. After returning the reaction solution to room temperature, water and chloroform were added and extracted. The organic layer was washed with brine, dried over anhydrous sodium sulphate, and evaporated under reduced pressure. The residue was purified by column chromatograph on silica gel (methylene chloride) to give 2-chloro-5-phenylthiazole as pale yellow crystal (0.68 g; 62%).

後処理

  1. temperaturecooling
  2. customto room temperature
  3. extractionextracted
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatograph on silica gel (methylene chloride)

出典と根拠

ORDレコード
ord-cd1d8a8bf6ed4261b678782bee45a637
出典データセット
uspto-grants-2012_01
特許番号
US08097610B2

関連ノート

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