Dicyclohexylcarbodiimide → HCID 19816117, compound
Reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:10]([O:11][CH3:12])=[CH:9][C:8]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=O)=[CH:7][C:6]=1[O:20][CH3:21].[SH:22][C:23]1[S:24][CH2:25][CH2:26][N:27]=1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([O:20][CH3:21])=[CH:7][C:8]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([N:27]2[CH2:26][CH2:25][S:24][C:23]2=[S:22])=[O:19])=[CH:9][C:10]=1[O:11][CH3:12]Participants
6
Procedure
To a solution of 0.88 g of 5-(4-methoxymethoxy-3,5-dimethoxyphenyl)pentanoic acid and 0.42 g of 2-mercaptothiazoline in 30 ml of dichloromethane were added 0.73 g of dicyclohexylcarbodiimide and 36 mg of 4-dimethylaminopyridine at room temperature followed by stirring for 16 hours. The reaction mixture was filtered with suction, and the filtrate washed with a 1N aqueous NaOH solution and then with saturated aqueous sodium chloride and dried over sodium sulfate. The solvent was removed by distillation, and the residue subjected to column chromatography on silica gel. From the fraction eluted with dichloromethane was obtained 1.15 g of N-[5-(4-methoxymethoxy-3,5-dimethoxyphenyl)pentanoyl)-thiazolidine-2-thione.
Workup
- filtrationThe reaction mixture was filtered with suction
- washthe filtrate washed with a 1N aqueous NaOH solution
- dry with materialwith saturated aqueous sodium chloride and dried over sodium sulfate
- customThe solvent was removed by distillation
- washFrom the fraction eluted with dichloromethane
Sources & evidence
- ORD record
- ord-310167265cf241e89ecfa6f43edd6585
- Source dataset
- uspto-grants-1991_08
- Patent number
- US05037837
Reaction notes
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