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

HRID 378802

반응식

HRID 378802 반응식
[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]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 996PhenolHCID 14798Sodium HydroxideHCID 15965Picloram

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3bf316338c504e9f9a449d19bfd56465
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06297197B1

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