Benzylethanolamine → N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide

HRID 886888노트

반응식

HRID 886888 반응식
[Br:1][C:2]1[C:7]([C:8]([OH:10])=O)=[C:6]([F:11])[CH:5]=[CH:4][CH:3]=1.CN(C)C=O.[CH2:17]([NH:24][CH2:25][CH2:26][OH:27])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(N(CC)CC)C>S(Cl)(Cl)=O.O1CCCC1.O>[CH2:17]([N:24]([CH2:25][CH2:26][OH:27])[C:8](=[O:10])[C:7]1[C:2]([Br:1])=[CH:3][CH:4]=[CH:5][C:6]=1[F:11])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

8

반응물 4

HCID 4348BenzylethanolamineHCID 6228DimethylformamideHCID 8471TriethylamineHCID 3026212-Bromo-6-fluorobenzoic acid

생성물 1

HCID 68578409N-benzyl-6-bromo-2-fluoro-N-(2-hydroxyethyl)benzamide수율 97.5%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 24386Thionyl Chloride용매

실험 절차

A solution of 6-bromo-2-fluorobenzoic acid (10.0 g, 45.7 mmol) and N,N-dimethylformamide (0.100 ml) in thionylchloride (40 ml) was stirred at 85° C. for 12 hr, and the solvent was evaporated under reduced pressure. The residue was added to a solution of N-benzylethanolamine (6.91 g, 45.7 mmol) and triethylamine (9.55 ml, 68.6 mmol) in tetrahydrofuran (100 ml) under ice-cooling, and the mixture was stirred for 1 hr under ice-cooling and at room temperature for 1 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the desired product (15.7 g, 97.5%) as an oil.

후처리

  1. customthe solvent was evaporated under reduced pressure
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-b82cc26e824f49f7b8f03f60f8669ead
출처 데이터셋
uspto-grants-2012_08
특허 번호
US08247403B2

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