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

HRID 378240

反応式

HRID 378240 の反応式
[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

参加物

7

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-26f784be0e59469797b42eadcca21f48
出典データセット
uspto-grants-2000_02
特許番号
US06030969

関連ノート

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