Triethylamine → 3-Hydroxy-4-methoxy-4'-benzyloxypicolinanilide

HRID 350641

反応式

HRID 350641 の反応式
Cl.[CH2:2]([O:9][C:10]1[CH:16]=[CH:15][C:13]([NH2:14])=[CH:12][CH:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Cl.[OH:18][C:19]1[C:20]([C:27](O)=[O:28])=[N:21][CH:22]=[CH:23][C:24]=1[O:25][CH3:26].ON1C2C=CC=CC=2N=N1.C(N(CC)CC)C.CCN=C=NCCCN(C)C.Cl>C(Cl)(Cl)Cl>[OH:18][C:19]1[C:20]([C:27]([NH:14][C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:2][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)=[CH:16][CH:15]=2)=[O:28])=[N:21][CH:22]=[CH:23][C:24]=1[O:25][CH3:26]

参加物

7

反応物 5

HCID 8471Triethylamine2 回HCID 757711-HydroxybenzotriazoleHCID 27238314-Benzyloxyaniline hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 694976023-Hydroxy-4-methoxypicolinic acid hydrochloride

生成物 1

HCID 155150083-Hydroxy-4-methoxy-4'-benzyloxypicolinanilide収率 59%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

4-Benzyloxyaniline hydrochloride (0.21 g, 0.87 mmol), 0.15 g (0.73 mmol) of 3-hydroxy-4-methoxypicolinic acid hydrochloride, 0.15 g (1.10 mmol) of 1-hydroxybenzotriazole, and 0.16 g (1.10 mmol) of triethylamine were mixed into chloroform to prepare a suspension (2 ml). A chloroform solution (2 ml) of WSCI.HCl (0.21 g, 1.10 mmol) and 0.11 g (1.10 mmol) of triethylamine were added dropwise at −20° C. to this suspension, and a reaction was then allowed to proceed at room temperature overnight. The reaction mixture was concentrated under the reduced pressure. The concentrate was redissolved in chloroform. The solution was washed with saturated brine, and was then dried over anhydrous sodium sulfate. The dried solution was concentrated under the reduced pressure. The residue was purified by column chromatography on silica gel (chloroform) to give 0.15 g (yield 59%) of title compound.

後処理

  1. concentrationThe reaction mixture was concentrated under the reduced pressure
  2. dissolutionThe concentrate was redissolved in chloroform
  3. washThe solution was washed with saturated brine
  4. dry with materialwas then dried over anhydrous sodium sulfate
  5. concentrationThe dried solution was concentrated under the reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (chloroform)

出典と根拠

ORDレコード
ord-d133d006350943dbb74c6d34a66b4024
出典データセット
uspto-grants-2007_02
特許番号
US07183278B1

関連ノート

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