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

HRID 420547

반응식

HRID 420547 반응식
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

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 61482Cupric chloride dihydrate촉매HCID 962Water용매HCID 6212Chloroform용매

반응 조건

온도
40 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-cd1d8a8bf6ed4261b678782bee45a637
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08097610B2

연결된 노트

불러오는 중…