RU 25591 → HCID 131711660、化合物

HRID 1447655ノート

反応式

HRID 1447655 の反応式
N(C(OCC)=O)=NC(OCC)=O.[CH3:13][N:14](C)[C@@H:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[C@H:17]([O:26][C:27]2[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=2)[CH2:16]1>CC(C)=O>[CH3:13][NH:14][C@@H:15]1[CH2:21][CH2:20][C:19]2[CH:22]=[CH:23][CH:24]=[CH:25][C:18]=2[C@H:17]([O:26][C:27]2[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=2)[CH2:16]1

参加物

4

反応物 2

HCID 182578RU 25591HCID 220568ethyl N-ethoxycarbonyliminocarbamate

生成物 1

HCID 131711660HCID 131711660、化合物収率 64.1%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

348 mg of diethyl azocarboxylate were added to a mixture of 652 mg of cis N,N-dimethyl-5-[4-nitrophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine in 10 ml of acetone and the mixture was refluxed for 31/2 hours. The acetone was distilled under reduced pressure and 5 ml of N hydrochloric acid were added to the residue. The mixture was stirred at room temperature for 26 hours and was then made alkaline with ammonium hydroxide. The mixture was extracted with methylene chloride and the organic phase was washed with water, dried over magnesium sulfate and filtered. The filtrate was evaporated to dryness under reduced pressure to obtain 1.1 g of raw product which was chromatographed over silica gel. Elution with a 7-3 chloroform-methanol mixture yielded 400 mg of cis N-methyl-5-[4-nitrophenoxy]-6,7,8,9-tetrahydro-5H-benzocyclohepten-7-amine. The said product was dissolved in ethyl acetate containing gaseous hydrogen chloride and 380 mg of the hydrochloride of the cis compound melting at 265° C. was recovered therefrom.

後処理

  1. temperaturethe mixture was refluxed for 31/2 hours
  2. distillationThe acetone was distilled under reduced pressure and 5 ml of N hydrochloric acid
  3. additionwere added to the residue
  4. extractionThe mixture was extracted with methylene chloride
  5. washthe organic phase was washed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customThe filtrate was evaporated to dryness under reduced pressure
  9. customto obtain 1.1 g of raw product which
  10. customwas chromatographed over silica gel
  11. washElution with a 7-3 chloroform-methanol mixture

出典と根拠

ORDレコード
ord-4bd5f7802bc949ca8699b97d8b8e815e
出典データセット
uspto-grants-1979_12
特許番号
US04177292

反応ノート

読み込み中…