(3,4-Dimethoxyphenyl)acetic acid → 2-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide

HRID 378240

반응식

HRID 378240 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:11][C:12]([OH:14])=O)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1.C(N(CC)CC)C.Cl.[CH3:44][NH:45][O:46][CH3:47]>C(Cl)Cl>[CH3:44][N:45]([O:46][CH3:47])[C:12](=[O:14])[CH2:11][C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

7

반응물 5

HCID 7139(3,4-Dimethoxyphenyl)acetic acidHCID 8471TriethylamineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

생성물 1

HCID 112186512-(3,4-dimethoxyphenyl)-N-methoxy-N-methylacetamide수율 66.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(3,4-Dimethoxyphenyl)acetic acid (13.0 g, 66.4 mmol) was suspended in anhydrous CH2Cl2 followed by addition of EDCI (15.3 g, 79.7 mmol), HOBt (20.6 g, 152 mmol), triethylamine (8.06 g, 79.7 mmol), and N,O-dimethylhydroxylamine hydrochloride (6.48 g, 66.4 mmol). The reaction was stirred 3 days at ambient temperature after which the solvent was evaporated at reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with aq. HCl, sat NaHCO3, brine, dried (Na2SO4), and concentrated in vacuo to give 10.5 g (66%) of N-methyl-N-methoxy-(3,4-dimethoxyphenyl)acetamide as a pale brown oil.

후처리

  1. customwas evaporated at reduced pressure
  2. customThe residue was partitioned between EtOAc and water
  3. washThe organic layer was washed with aq. HCl
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-26f784be0e59469797b42eadcca21f48
출처 데이터셋
uspto-grants-2000_02
특허 번호
US06030969

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