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 25088ノート

反応式

HRID 25088 の反応式
[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

参加物

5

反応物 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

生成物 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]benzodiazepine収率 42%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-695c86f66ffc4bbdaaff243f5c4f5faf
出典データセット
uspto-grants-2005_02
特許番号
US06858605B2

反応ノート

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