Diethyl Ether → N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

HRID 465913ノート

反応式

HRID 465913 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH2:14][CH2:15][CH3:16])=[C:12]([O:17][CH3:18])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=O.C1(N=C=NC2CCCCC2)CCCCC1.[S:34]1[CH2:38][CH2:37][NH:36][CH2:35]1.C(OCC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]([CH2:14][CH2:15][CH3:16])=[C:12]([O:17][CH3:18])[CH:11]=[CH:10][C:6]=1[C:7]([N:36]1[CH2:37][CH2:38][S:34][CH2:35]1)=[O:9]

参加物

7

反応物 4

HCID 3283Diethyl EtherHCID 10444ThiazolidineHCID 10868DicyclohexylcarbodiimideHCID 147195022-Methoxymethoxy-3-n-propyl-4-methoxybenzoic acid

生成物 1

HCID 14719505N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

Under argon atmosphere, a solution of 2-methoxymethoxy-3-n-propyl-4-methoxybenzoic acid (8 g) and 4-dimethylaminopyridine (0.38 g) in methylene chloride (150 ml) was cooled to 0° C., and to the solution was added N,N'-dicyclohexylcarbodiimide (7.8 g). The mixture was agitated for 15 minutes. Thiazolidine (3.0 ml) was added to the mixture, and the mixture was agitated at room temperature for another 15 hours. To the reaction mixture was added diethyl ether, and the mixture was filtered. Water and 1N aqueous hydrochloric acid were added to the filtrate, and the mixture was extracted with methylene chloride. The organic layer was washed with saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and concentrated in evacuated atomosphere. The residue was subjected to column chromatography using silica gel. There was obtained N-(2-methoxymethoxy-3-n-propyl-4-methoxybenzoyl)thiazolidine (9.0 g) from fractions eluted with n-hexane-ethyl acetate (2:1).

後処理

  1. stirringthe mixture was agitated at room temperature for another 15 hours
  2. filtrationthe mixture was filtered
  3. additionWater and 1N aqueous hydrochloric acid were added to the filtrate
  4. extractionthe mixture was extracted with methylene chloride
  5. washThe organic layer was washed with saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in evacuated atomosphere

出典と根拠

ORDレコード
ord-50d43c9e50374ac499905adb6fc803a2
出典データセット
uspto-grants-1992_10
特許番号
US05155106

反応ノート

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