Ethyl orthoformate → 4-bromo-3-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide

HRID 1593770노트

반응식

HRID 1593770 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:19]=[CH:20][C:21]([Br:26])=[C:22]([O:24][CH3:25])[CH:23]=1.[CH2:27](OC(OCC)OCC)C>C(O)(C)C>[Br:26][C:21]1[CH:20]=[CH:19][C:18]([NH:17][CH:27]=[C:3]([C:1]#[N:2])[C:4]([NH:6][C:7]2[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=2[Cl:16])=[O:5])=[CH:23][C:22]=1[O:24][CH3:25]

참가 물질

5

반응물 3

HCID 31214Ethyl orthoformate2회HCID 70182544-Bromo-3-methoxyanilineHCID 160991782-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

생성물 1

HCID 693122584-bromo-3-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide수율 73.2%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

To a suspension of 2-cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide (6.1 g, 23.5 mmol) in 500 mL of isopropanol was added 5-amino-2-bromoanisole (5.0 g, 24.8 mmol). This mixture was heated to reflux to give a clear yellow solution. To this solution, triethylorthoformate (10.6 mL, 63.5 mmol) was added dropwise and the reaction mixture was heated at reflux for 5 hours. An additional 10.6 mL of triethylorthoformate was added and the mixture was heated at reflux overnight. The mixture was allowed to cool to room temperature. The solid was collected by filtration, washed with isopropanol and ethyl acetate, and then dried overnight at ˜40° C. under reduced pressure to give 8.1 g (73%) of 4-bromo-3-methoxyanilino-N-(2,4-dichloro-5-methoxyphenyl)-2-cyano-2-propenamide as a yellow solid, mp >250° C.; MS (ES) m/z470.0, 472.0 (M+H)+

후처리

  1. temperatureThis mixture was heated
  2. temperatureto reflux
  3. customto give a clear yellow solution
  4. temperaturethe reaction mixture was heated
  5. temperatureat reflux for 5 hours
  6. temperaturethe mixture was heated
  7. temperatureat reflux overnight
  8. filtrationThe solid was collected by filtration
  9. washwashed with isopropanol and ethyl acetate
  10. customdried overnight at ˜40° C. under reduced pressure

출처 및 근거

ORD 기록
ord-2a5b7e23e3524c69bccccc1f329c4660
출처 데이터셋
uspto-grants-2007_11
특허 번호
US07297795B2

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