Triphenylphosphine → 4-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methoxy-butoxy)-benzamide

HRID 620284

反応式

HRID 620284 の反応式
[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:14][CH3:15])[CH2:12][CH3:13])=[O:7])=[C:4]([OH:19])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:39][O:40][CH:41]([CH3:45])[CH2:42][CH2:43]O.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[NH2:1][C:2]1[C:17]([Cl:18])=[CH:16][C:5]([C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:12][CH3:13])[CH2:14][CH3:15])=[O:7])=[C:4]([O:19][CH2:43][CH2:42][CH:41]([O:40][CH3:39])[CH3:45])[CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 172913-Methoxy-1-butanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 9817332o-Desmethyl metoclopramide

生成物 1

HCID 99293764-Amino-5-chloro-N-(2-diethylamino-ethyl)-2-(3-methoxy-butoxy)-benzamide収率 52.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A stirred solution of 4-amino-5-chloro-N-[2-(diethylamino)ethyl]-2-hydroxybenzamide (1.715 g, 6 mmoles; prepared according to Preparation 1B), triphenylphosphine (1.58 g, 6 mmoles), 3-methoxy-1-butanol (0.62 g, 6 mmoles) in dry tetrahydrofuran (50 ml) was treated dropwise with diethyl azodicarboxylate (1.1 g of 95% purity material, 6 mmoles). The solution was left to stir overnight. After evaporation of the solvent the residue was dissolved in methylene chloride. The solution was washed with 0.4N NaOH, water, dried and the solvent evaporated. The residue was chromatographed over deactivated silica using methylene chloride (100), methanol (2.5), ammonium hydroxide (0.5) solvent system. The appropriate fractions were combined and the solvent evaporated. The residue (1.7 g) was crystallized from toluene to yield 1.17 g (52%) of the title compound, m.p. 76°-78° C.

後処理

  1. waitThe solution was left
  2. customAfter evaporation of the solvent the residue
  3. dissolutionwas dissolved in methylene chloride
  4. washThe solution was washed with 0.4N NaOH, water
  5. customdried
  6. customthe solvent evaporated
  7. customThe residue was chromatographed over deactivated silica
  8. customthe solvent evaporated
  9. customThe residue (1.7 g) was crystallized from toluene

出典と根拠

ORDレコード
ord-56c9973285944906806d04864c153888
出典データセット
uspto-grants-1989_04
特許番号
US04820715

関連ノート

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