Phosphorus pentachloride → 1-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazole

HRID 1750912노트

반응식

HRID 1750912 반응식
Cl[CH2:2][CH2:3][NH:4][C:5](=O)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.P(Cl)(Cl)(Cl)(Cl)Cl.[CH:19]([C:22]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:25]2[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[C:23]=1[NH2:38])([CH3:21])[CH3:20]>C1(C)C=CC=C(C)C=1>[CH:19]([C:22]1[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[C:25]2[O:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=3[C:24]=2[C:23]=1[N:38]1[CH2:2][CH2:3][N:4]=[C:5]1[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)([CH3:21])[CH3:20]

참가 물질

5

반응물 3

HCID 24819Phosphorus pentachlorideHCID 101439N-(2-chloroethyl)benzamideHCID 584010762,4-Diisopropyldibenzo[b,d]furan-1-amine

생성물 1

HCID 584010671-(2,4-diisopropyldibenzo[b,d]furan-1-yl)-2-phenyl-4,5-dihydro-1H-imidazole수율 90.1%

시약·촉매·용매 1

HCID 7929M-Xylene용매

실험 절차

N-(2-chloroethyl)benzamide (2.1 g, 11.2 mmol), PCl5 (3.5 g, 16.8 mmol) were dissolved in m-Xylene (100 mL) and refluxed for 2 h. After cooling down the reaction flask to room temperature, 2,4-diisopropyldibenzo[b,d]furan-1-amine (3.3 g, 12.3 mmol) was added to it and the reaction mixture was refluxed overnight. From the cooled reaction mixture white precipitate was filtered out. Precipitate was dissolved in ethylacetate and partitioned between ethylacetate and aqueous Na2CO3. Organic phase was extracted out and dried under vacuum. Target compound (4 g, 90% yield) was used in next step without further purification.

후처리

  1. temperaturerefluxed for 2 h
  2. temperaturethe reaction mixture was refluxed overnight
  3. customFrom the cooled reaction mixture white precipitate
  4. filtrationwas filtered out
  5. dissolutionPrecipitate was dissolved in ethylacetate
  6. custompartitioned between ethylacetate and aqueous Na2CO3
  7. extractionOrganic phase was extracted out
  8. customdried under vacuum

출처 및 근거

ORD 기록
ord-5e0b1c1a09db455f9220f5360161149f
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09156870B2

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