p-Anisoyl chloride → 4-Methoxy-N-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)benzamide

HRID 1017872노트

반응식

HRID 1017872 반응식
[CH3:1][C:2]1([CH3:21])[CH:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:5]2[C:13]([CH3:20])=[C:14]([NH2:19])[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]=2[O:3]1.[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28](Cl)=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[CH3:22][O:23][C:24]1[CH:32]=[CH:31][C:27]([C:28]([NH:19][C:14]2[C:15]([CH3:18])=[C:16]([CH3:17])[C:4]3[O:3][C:2]([CH3:21])([CH3:1])[CH:6]([C:7]4[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=4)[C:5]=3[C:13]=2[CH3:20])=[O:29])=[CH:26][CH:25]=1

참가 물질

5

반응물 3

HCID 7477p-Anisoyl chlorideHCID 8471TriethylamineHCID 105407985-Amino-2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydrobenzofuran

생성물 1

HCID 101801024-Methoxy-N-(2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-yl)benzamide수율 72%

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a solution of 2,2,4,6,7-pentamethyl-3-phenyl-2,3-dihydro-1-benzofuran-5-amine (1.60 g, 5.69 mmol) and 4-methoxybenzoyl chloride (1.16 g, 6.82 mmol) in chloroform (20 ml) was added triethylamine (0.87 ml, 6.26 mmol) and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure. Water (30 ml) was added into the residue and the product was extracted twice with ethyl acetate. The combined organic layers were washed with 1N hydrochloric acid and an aqueous, saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from methanol to obtain 1.70 g (72% yield) of the title compound. Melting point: 190-192° C.

후처리

  1. customThe solvent was removed under reduced pressure
  2. additionWater (30 ml) was added into the residue
  3. extractionthe product was extracted twice with ethyl acetate
  4. washThe combined organic layers were washed with 1N hydrochloric acid
  5. dry with materialan aqueous, saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol

출처 및 근거

ORD 기록
ord-af2b2c38b26d4ba283e0606ee6cd7b8c
출처 데이터셋
uspto-grants-2002_11
특허 번호
US06479536B1

반응 노트

불러오는 중…