Benzylamine → HCID 20353220, 화합물

HRID 372092

반응식

HRID 372092 반응식
[CH2:1]([NH2:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:9]1[C:22]2[C:13](=[CH:14][C:15]3[C:20]([C:21]=2[C:23](Cl)=[O:24])=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:12]=[CH:11][CH:10]=1.[O:26]1CCCC1>>[C:1]([NH:8][C:23]([C:21]1[C:22]2[C:13]([CH:14]=[C:15]3[C:20]=1[CH:19]=[CH:18][CH:17]=[CH:16]3)=[CH:12][CH:11]=[CH:10][CH:9]=2)=[O:24])(=[O:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 3

HCID 7504BenzylamineHCID 8028Tetrahydrofuran2회HCID 167528Anthracene-9-carbonyl chloride

생성물 1

HCID 20353220HCID 20353220, 화합물

실험 절차

To a mixture of 30 ml of benzylamine and 60 ml of tetrahydrofuran is added dropwise with cooling, a solution of 9.86 g of 9-anthroyl chloride in 30 ml of tetrahydrofuran. After stirring at room temperature overnight, the mixture is concentrated, and the residue is dissolved in methylene chloride. The solution is washed with dilute acid and dilute base, dried, and concentrated to give 12.45 g of crude N-benzoyl-9-anthramide. The product is added to a slurry of 2.50 g of sodium hydride (50% in oil, previously washed with hexane) in 80 ml of tetrahydrofuran and the mixture is heated to reflux for 30 min and cooled. Propargyl bromide (6.0 g) in 10 ml of tetrahydrofuran is added, and the reaction mixture is heated under reflux for 2 hours. Water and methylene chloride are added; the layers are separated, and the dried organic layer is concentrated. The residue (crude N-benzyl-N-propargyl-9-anthramide) is heated under reflux with 100 ml of p-xylene for 2.5 hr. On cooling, 9.81 g of 2-benzyl-3,5-dihydro-5,9b-o-benzenobenz [e]isoindol-1-(2H)-one precipitates.

후처리

  1. additionis added dropwise
  2. temperaturewith cooling
  3. concentrationthe mixture is concentrated
  4. dissolutionthe residue is dissolved in methylene chloride
  5. washThe solution is washed
  6. additionwith dilute acid
  7. additiondilute base
  8. customdried
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-e93bc74008074d3faa8312f00ac6bc9d
출처 데이터셋
uspto-grants-1978_05
특허 번호
US04088772

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