Dimethyl Sulfoxide → Methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate

HRID 378802

反応式

HRID 378802 の反応式
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6](Cl)[N:5]=[C:4]([C:10]([OH:12])=[O:11])[C:3]=1[Cl:13].[C:14]1([OH:20])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[OH-].[Na+].[CH3:23]S(C)=O>O>[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:20][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[N:5]=[C:4]([C:10]([O:12][CH3:23])=[O:11])[C:3]=1[Cl:13]

参加物

6

反応物 4

HCID 679Dimethyl SulfoxideHCID 996PhenolHCID 14798Sodium HydroxideHCID 15965Picloram

生成物 1

HCID 21696627Methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate収率 14%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

実験手順

A solution of 4-amino-3,5,6-trichloropyridine-2-carboxylic acid (7.2 g, 0.03 mol), phenol (3.0 g, 0.036 mol) and sodium hydroxide (2.7 g 0.068 mol) in DMSO (60 mL) and water (9 mL) was heated to 130° C. for 18 hr. The reaction was diluted with water (250 mL) and a tacky solid collected. This material was dissolved in methanol (100 mL) and treated with TMSCHN2 (25 mL 2M in hexanes). The reaction was stirred 30 min and concentrated. The resulting oil was chromatographed over silica gel (80% hexane and 20% ethyl acetate) to give methyl 4-amino-3,5-dichloro-6-phenoxypyridine-2-carboxylate (1.2, g, 14%); mp 88-90° C.

後処理

  1. customa tacky solid collected
  2. dissolutionThis material was dissolved in methanol (100 mL)
  3. additiontreated with TMSCHN2 (25 mL 2M in hexanes)
  4. concentrationconcentrated
  5. customThe resulting oil was chromatographed over silica gel (80% hexane and 20% ethyl acetate)

出典と根拠

ORDレコード
ord-3bf316338c504e9f9a449d19bfd56465
出典データセット
uspto-grants-2001_10
特許番号
US06297197B1

関連ノート

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