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

HRID 886888ノート

反応式

HRID 886888 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 24386Thionyl Chloride溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b82cc26e824f49f7b8f03f60f8669ead
出典データセット
uspto-grants-2012_08
特許番号
US08247403B2

反応ノート

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