Diisopropylethylamine → Methyl 4-[(5-bromo-2-methyl-benzoyl)amino]-3,5-dimethyl-benzoate

HRID 239936

反応式

HRID 239936 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[NH2:12][C:13]1[C:22]([CH3:23])=[CH:21][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:15][C:14]=1[CH3:24].C(N(CC)C(C)C)(C)C.CCCP1(OP(CCC)(=O)OP(CCC)(=O)O1)=O>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[C:14]([CH3:24])=[CH:15][C:16]([C:17]([O:19][CH3:20])=[O:18])=[CH:21][C:22]=1[CH3:23])=[O:9]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 111923Propylphosphonic anhydrideHCID 3460045-Bromo-2-methylbenzoic acidHCID 11030398Benzoic acid, 4-amino-3,5-dimethyl-, methyl ester

生成物 1

HCID 86707323Methyl 4-[(5-bromo-2-methyl-benzoyl)amino]-3,5-dimethyl-benzoate収率 107.9%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 5-bromo-2-methylbenzoic acid (2.0 g, 0.008 mol) in CH2Cl2 (20 mL) at 0° C. are added methyl 4-amino-3,5-dimethylbenzoate (1.28 g, 0.0072, see preparation 12) and N,N-diisopropylethylamine (4.12 g, 0.032 mol). After stirring the reaction mixture for 10 minutes, 1-propanephosphonic acid cyclic anhydride (50% solution in ethyl acetate, 7.63 g, 0.024 mol) is added via syringe and stirred at 50° C. After 16 hours, the solvent is removed under reduced pressure and the residue is diluted with water and extracted twice with ethyl acetate. The organic layers are combined and dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting residue is purified by flash chromatography (silica gel) using 12% ethyl acetate in hexane to give the title compound as a white solid (2.9 g, 97%). Mass spectrum (m/z): 376.0 (M+1).

後処理

  1. stirringstirred at 50° C
  2. waitAfter 16 hours
  3. customthe solvent is removed under reduced pressure
  4. additionthe residue is diluted with water
  5. extractionextracted twice with ethyl acetate
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe resulting residue is purified by flash chromatography (silica gel)

出典と根拠

ORDレコード
ord-5df3b57330d74beebb2026f05a5b940b
出典データセット
uspto-grants-2014_02
特許番号
US08642768B2

関連ノート

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