Potassium Carbonate → {2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester

HRID 448861노트

반응식

HRID 448861 반응식
[Br:1][C:2]1[CH:3]=[C:4]([CH:16]=[CH:17][C:18]=1[Cl:19])[C:5]([N:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[OH:15])[CH3:8])=[O:6].[CH3:20][O:21][C:22](=[O:25])[CH2:23]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:20][O:21][C:22](=[O:25])[CH2:23][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:7]([C:5](=[O:6])[C:4]1[CH:16]=[CH:17][C:18]([Cl:19])=[C:2]([Br:1])[CH:3]=1)[CH3:8]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 686031173-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide

생성물 1

HCID 68602946{2-[(3-Bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester수율 92.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-bromo-4-chloro-N-(2-hydroxy-phenyl)-N-methyl-benzamide (442 mg, 1.3 mmol), methylbromoacetate (0.247 mL, 2.6 mmol) and K2CO3 (717 mg, 5.2 mmol) was heated in DMF (8 mL) at 80° C. for 5 hrs. After cooling to room temperature, the mixture was partitioned between ethyl acetate and water. The organic layer was separated and washed with brine, dried over Na2SO4, then purified by silica gel column chromatography eluted with ethyl acetate/hexane (1/4) to yield {2-[(3-bromo-4-chloro-benzoyl)-methyl-amino]-phenoxy}-acetic acid methyl ester (495 mg). MS [M+H]+: 413.9; tR=2.75 min. (method 1)

후처리

  1. customthe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. custompurified by silica gel column chromatography
  6. washeluted with ethyl acetate/hexane (1/4)

출처 및 근거

ORD 기록
ord-dc19c1b9147447778c50b5771a0b706d
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481738B2

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