Triphenylphosphine → (+/-)-7-(3-Chloropyridazin-6-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine

HRID 25088노트

반응식

HRID 25088 반응식
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][N:9]=[C:10]([C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=2)[C:11]2[C:12]([CH2:20][CH:21](O)[CH3:22])=[CH:13][C:14]3[O:18][CH2:17][O:16][C:15]=3[CH:19]=2)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>CN(C)C=O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:21]([CH3:22])[CH2:20][C:12]3[CH:13]=[C:14]4[O:18][CH2:17][O:16][C:15]4=[CH:19][C:11]=3[C:10]([C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)=[N:9]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 865938171-(6-[(6-Chloropyridazin-3-yl)-hydrazono-(4-nitrophenyl)-methyl]-(benzo-1,3-dioxol-5-yl)}-propan-2-ol

생성물 1

HCID 22565518(+/-)-7-(3-Chloropyridazin-6-yl)-8-methyl-5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine수율 42%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 0.3 g (0.66 mmol) of the compound prepared in Step A, 10 ml of dimethylformamide and 0.34 g (1.30 mmol) of triphenyiphosphine was stirred at room temperature for 5 min, then 0.20 ml (1.27 mmol) of diethyl azodicarboxylate was added and stirring was continued for 24 h. After dilution with sodium chloride solution the precipitated product was filtered off, dried and purified by column chromatography using silica gel (MN Kieselgel 60) as adsorbent and a mixture of chloroform-methanol (99:1) as eluent. The residue obtained on concentration was crystallized by refluxing in ethanol to yield 0.12 g (42%) of the title compound; Mp.: 254-255° C.

후처리

  1. stirringstirring
  2. waitwas continued for 24 h
  3. filtrationAfter dilution with sodium chloride solution the precipitated product was filtered off
  4. customdried
  5. custompurified by column chromatography
  6. additiona mixture of chloroform-methanol (99:1) as eluent
  7. customThe residue obtained on concentration
  8. customwas crystallized
  9. temperatureby refluxing in ethanol

출처 및 근거

ORD 기록
ord-695c86f66ffc4bbdaaff243f5c4f5faf
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06858605B2

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