1,1'-Carbonyldiimidazole → 3-(4-Bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide

HRID 1527963노트

반응식

HRID 1527963 반응식
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH2:9][C:10](O)=[O:11])=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[CH3:33][NH:34][O:35][CH3:36]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH3:19])[CH2:9][C:10]([N:34]([O:35][CH3:36])[CH3:33])=[O:11])=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 682631,1'-CarbonyldiimidazoleHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 670156223-(4-Bromophenyl)-3-o-tolylpropanoic acid

생성물 1

HCID 866609493-(4-Bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide수율 89.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a suspension of 3-(4-bromophenyl)-3-o-tolylpropanoic acid (125.5 g, 393 mmol) in dichloromethane (600 mL) was added 1,1′-carbonyldiimidazole (79.7 g, 491 mmol) portionwise over 5 min. After gas evolution had ceased N,O-dimethylhydroxylamine hydrochloride (42.2 g, 432 mmol) was added in portions over 5 min. The reaction mixture was stirred for 17 h at room temperature, then washed with water. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. The crude product was chromatographed (SiO2; heptane/ethyl acetate 3:1) and the product triturated with heptane to produce the title compound (127 g, 88%). White solid, MS: 362.1 [M+H]+.

후처리

  1. additionwas added in portions over 5 min
  2. washwashed with water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe crude product was chromatographed (SiO2; heptane/ethyl acetate 3:1)
  8. customthe product triturated with heptane

출처 및 근거

ORD 기록
ord-935fcff1334e4ec8bf5a45f97b48770e
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09090565B2

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