Acetonitrile → Sodium 2-cyano-1-(1,3-thiazol-5-yl)ethenolate

HRID 1055690

반응식

HRID 1055690 반응식
[S:1]1[C:5]([C:6]([O:8]C)=O)=[CH:4][N:3]=[CH:2]1.[C:10](#[N:12])[CH3:11].[H-].[Na+:14].C(OC)(C)(C)C>C1COCC1>[C:10]([CH:11]=[C:6]([C:5]1[S:1][CH:2]=[N:3][CH:4]=1)[O-:8])#[N:12].[Na+:14]

참가 물질

6

반응물 4

HCID 6342AcetonitrileHCID 15413tert-Butyl methyl etherHCID 24758Sodium hydrideHCID 331117Methyl 1,3-thiazole-5-carboxylate2회

생성물 1

HCID 86690968Sodium 2-cyano-1-(1,3-thiazol-5-yl)ethenolate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1.5 g (10.5 mmol) of methyl 1,3-thiazole-5-carboxylate and 430 mg (10.8 mmol) of acetonitrile in 15 ml of THF was added dropwise to a suspension of 419 mg of sodium hydride (60% strength suspension in mineral oil) in 16 ml of THF which was heated under reflux. The reaction mixture was heated under reflux for 20 h. After cooling, 50 ml of methyl tert-butyl ether were added and the mixture was stirred for 30 minutes. The resulting precipitate was filtered off with suction through a frit and dried under oil pump vacuum. This gave 1.71 g (94% of theory) of the title compound which was combined with the product (3.48 g, 95% of theory) from a second batch starting with 3.0 g (21 mmol) of methyl 1,3-thiazole-5-carboxylate. This material was used without further characterization for the next step.

후처리

  1. temperaturewas heated
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureunder reflux for 20 h
  5. temperatureAfter cooling
  6. filtrationThe resulting precipitate was filtered off with suction through a frit
  7. customdried under oil pump vacuum

출처 및 근거

ORD 기록
ord-afcb85efea60443db2e684e976808815
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09394309B2

연결된 노트

불러오는 중…