Dicyclohexylcarbodiimide → HCID 19816115, compound

HRID 2247989Notes

Reaction equation

HRID 2247989 reaction equation
[SH:1][C:2]1[S:3][CH2:4][CH2:5][N:6]=1.C1(N=C=NC2CCCCC2)CCCCC1.[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34](O)=[O:35])=[CH:28][C:27]=1[O:37][CH3:38]>ClCCl.CN(C)C1C=CN=CC=1>[CH3:22][O:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][CH2:33][C:34]([N:6]2[CH2:5][CH2:4][S:3][C:2]2=[S:1])=[O:35])=[CH:28][C:27]=1[O:37][CH3:38]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 19816111HCID 19816111, compoundHCID 178527880HCID 178527880, compound

Product 1

HCID 19816115HCID 19816115, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

In an atmosphere of argon 4.03 g of 3-(4-methoxymethoxy-3-methoxyphenyl)propionic acid and 1.79 g of 2-mercaptothiazoline were dissolved in 80 ml of dichloromethane followed by the addition of 3.10 g of dicyclohexylcarbodiimide and 0.21 g of 4-dimethylaminopyridine. The mixture was stirred at room temperature for 15 hours, and the reaction mixture was filtered. The filtrate was washed with a 1N aqueous sodium hydroxide, water and saturated aqueous sodium chloride and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure, and the residue subjected to column chromatography on silica gel. From the fraction eluted with methylene chloride was obtained 5.07 g of N-[3-(4-methoxymethoxy-3-methoxyphenyl)propanoyl]-thiazolidine-2thione.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washThe filtrate was washed with a 1N aqueous sodium hydroxide, water and saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed by distillation under reduced pressure
  5. washFrom the fraction eluted with methylene chloride

Sources & evidence

ORD record
ord-878a539fb90647c8ae656df29e9c99bb
Source dataset
uspto-grants-1991_08
Patent number
US05037837

Reaction notes

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