Triethylamine → N-(2-hydroxy-2-phenylethyl)-3,5-dimethoxybenzamide

HRID 1976768노트

반응식

HRID 1976768 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([OH:8])=O.C1C=C2N=NN(O)C2=CC=1.O.CCN=C=NCCCN(C)C.C(N(CC)CC)C.[NH2:43][CH2:44][CH:45]([C:47]1[CH:52]=[C:51](OC)[C:50](OC)=[C:49](OC)[CH:48]=1)[OH:46]>ClCCl>[OH:46][CH:45]([C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)[CH2:44][NH:43][C:6](=[O:8])[C:5]1[CH:9]=[C:10]([O:12][CH3:13])[CH:11]=[C:3]([O:2][CH3:1])[CH:4]=1

참가 물질

7

반응물 5

HCID 8471TriethylamineHCID 143323,5-Dimethoxybenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 288942-Amino-1-(3,4,5-trimethoxyphenyl)ethanolHCID 27960291-Hydroxybenzotriazole hydrate

생성물 1

HCID 21998722N-(2-hydroxy-2-phenylethyl)-3,5-dimethoxybenzamide수율 94.3%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A suspension of 3,5-dimethoxybenzoic acid (1.00 g, 5.49 mmol) in dichloromethane (50 mL) at 0° C. was treated with HOBt hydrate (0.742 g, 5.49 mmol), stirred for 15 minutes, treated with EDCI (1.05 g, 5.49 mmol) in one portion, stirred for an additional 25 minutes, treated with triethylamine (1.84 g; 2.53 mL, 1.9 mmol) and the acetate salt of 2-amino-1-(3,4,5-trimethoxyphenyl)ethanol (1.58 g, 005.49 mmol), stirred for 18 hours while warming to room temperature, and concentrated. The concentrate was partitioned between ethyl acetate (400 mL) and water (200 mL), and the organic extract was washed sequentially with 10% KHSO4 (200 mL), water (100 mL), NaHCO3 (200 mL), and water (100 mL), dried (MgSO4), filtered, and concentrated to provide 1.56 g of the desired product as a white foamy semi-solid.

후처리

  1. stirringstirred for an additional 25 minutes
  2. concentrationconcentrated
  3. customThe concentrate was partitioned between ethyl acetate (400 mL) and water (200 mL)
  4. extractionthe organic extract
  5. washwas washed sequentially with 10% KHSO4 (200 mL), water (100 mL), NaHCO3 (200 mL), and water (100 mL)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-36ba17b6e39a493ba227457f28b989b9
출처 데이터셋
uspto-grants-2001_05
특허 번호
US06228868B1

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