Water → Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

HRID 1629879

反応式

HRID 1629879 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12].C(N(CC)CC)C.[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26](Cl)=[O:27].O>C1COCC1>[Cl:20][CH2:21][CH2:22][O:23][CH2:24][CH2:25][C:26]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[CH3:12])=[O:27]

参加物

6

反応物 4

HCID 962WaterHCID 8471TriethylamineHCID 2736799Methyl 4-amino-3-methylbenzoateHCID 860693723-(2-Chloroethoxy)propanoyl chloride

生成物 1

HCID 67048278Methyl 4-[3-(2-chloro-ethoxy)-propionyl-amino]-3-methyl-benzoate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

1.70 g (10.3 mmol) methyl 4-amino-3-methyl-benzoate in 10 ml THF are combined with 2.84 ml (20.6 mmol) triethylamine and stirred for 20 minutes at ambient temperature. Then a solution of 1.78 g (10.4 mmol) 3-(2-chloro-ethoxy)-propionic acid-chloride in 25 ml THF is added dropwise and the mixture is stirred for a further 2.5 hours at ambient temperature. Then water is added and the mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulphate and evaporated down completely i. vac. The residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3->6:4).

後処理

  1. stirringthe mixture is stirred for a further 2.5 hours at ambient temperature
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried over sodium sulphate
  4. customevaporated down completely
  5. customThe residue is purified by chromatography on silica gel (eluting gradient: petroleum ether/ethyl acetate=7:3->6:4)

出典と根拠

ORDレコード
ord-8e63cca2dad34161a4577676e874426d
出典データセット
uspto-grants-2014_07
特許番号
US08791103B2

関連ノート

読み込み中…