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

HRID 350641

반응식

HRID 350641 반응식
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]

참가 물질

7

반응물 5

HCID 8471Triethylamine2회HCID 757711-HydroxybenzotriazoleHCID 27238314-Benzyloxyaniline hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 694976023-Hydroxy-4-methoxypicolinic acid hydrochloride

생성물 1

HCID 155150083-Hydroxy-4-methoxy-4'-benzyloxypicolinanilide수율 59%

시약·촉매·용매 1

HCID 6212Chloroform용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d133d006350943dbb74c6d34a66b4024
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183278B1

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