Phosphorus oxide (P4O10) → 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide

HRID 661684ノート

反応式

HRID 661684 の反応式
[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[NH:17][CH3:18].O=P12OP3(OP(OP(O3)(O1)=O)(=O)O2)=O>C1(C)C(C)=CC=CC=1>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([N:17]([C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[O:14][CH3:13])[CH3:18])=[O:9]

参加物

5

反応物 3

HCID 14812Phosphorus oxide (P4O10)HCID 27595792-Methoxy-N-methylanilineHCID 110213535-Bromo-4-chloro-2-hydroxybenzoic acid

生成物 1

HCID 686025845-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide収率 44.7%

試薬・触媒・溶媒 1

HCID 7237O-Xylene溶媒

反応条件

温度
60 °C

実験手順

Alternatively, a mixture of 5-bromo-4-chloro-2-hydroxybenzoic acid (5 g, 19.9 mmol), 2-methoxy-N-methylaniline (3.13 g, 22.9 mmol) and P2O5 (5.36 g, 37.8 mmol) in anhydrous xylene was heated at 60° C. for 2 hrs and then refluxed for 17 hrs. The mixture was concentrated and purified via silica gel flash column chromatography eluted with ethyl acetate in hexane (20%) to give 5-bromo-4-chloro-2-hydroxy-N-(2-methoxy-phenyl)-N-methyl-benzamide (3.3 g).

後処理

  1. temperaturerefluxed for 17 hrs
  2. concentrationThe mixture was concentrated
  3. custompurified via silica gel flash column chromatography
  4. washeluted with ethyl acetate in hexane (20%)

出典と根拠

ORDレコード
ord-31dcf537ed50496b8efc32d695625be5
出典データセット
uspto-grants-2011_12
特許番号
US08084614B2

反応ノート

読み込み中…