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

HRID 465913Notes

Reaction equation

HRID 465913 reaction equation
[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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-50d43c9e50374ac499905adb6fc803a2
Source dataset
uspto-grants-1992_10
Patent number
US05155106

Reaction notes

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