Ethyl orthoformate → 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-(thien-3-ylamino)prop-2-enamide

HRID 1593772

반응식

HRID 1593772 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2].[NH2:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1.[CH2:23](OC(OCC)OCC)C>C(O)(C)C>[C:1]([C:3](=[CH:23][NH:17][C:18]1[CH:22]=[CH:21][S:20][CH:19]=1)[C:4]([NH:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[Cl:16])=[O:5])#[N:2]

참가 물질

5

반응물 3

HCID 31214Ethyl orthoformateHCID 640543thiophen-3-amine3회HCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

생성물 1

HCID 693136752-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-(thien-3-ylamino)prop-2-enamide수율 26%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (1.57 g, 6.06 mmol) in 200 mL of iso-propanol was added 3-aminothiophene (600 mg, 6.06 mmol). This mixture was heated to reflux and triethylorthoformate (6.5 mL, 39.1 mmol) was added dropwise. The reaction mixture was heated at reflux overnight. Additional 3-aminothiophene (214 mg, 2.16 mmol) was added and the reaction mixture was heated at reflux for 5 hours. Additional 3-aminothiophene (100 mg, 1.01 mmol) was added and the reaction mixture was heated at reflux for 2.5 hours. The mixture was allowed to cool to room temperature and the solid was collected by filtration, washed with iso-propanol to give 572 mg (26%) of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)-3-(thien-3-ylamino)prop-2-enamide as a tan solid, mp >250° C.; MS 366.0, 368.2 (M−H)−

후처리

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. temperatureThe reaction mixture was heated
  4. temperatureat reflux overnight
  5. temperaturethe reaction mixture was heated
  6. temperatureat reflux for 5 hours
  7. temperaturethe reaction mixture was heated
  8. temperatureat reflux for 2.5 hours
  9. filtrationthe solid was collected by filtration
  10. washwashed with iso-propanol

출처 및 근거

ORD 기록
ord-5a886353dd1545818b1b995b5618d85a
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297795B2

연결된 노트

불러오는 중…