Methanol → HCID 10997333, compound

HRID 2395242Notes

Reaction equation

HRID 2395242 reaction equation
[CH:1]1(N=C=NC2CCCCC2)CCCCC1.[O:16]=[C:17]1[S:21][CH2:20][CH:19]([C:22]([OH:24])=[O:23])[CH2:18]1.CO>C(OCC)C.CN(C1C=CC=CN=1)C>[CH3:1][O:23][C:22]([CH:19]1[CH2:18][C:17](=[O:16])[S:21][CH2:20]1)=[O:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 10868DicyclohexylcarbodiimideHCID 31539575-oxothiolane-3-carboxylic acid

Product 1

HCID 10997333HCID 10997333, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 218852-DimethylaminopyridineCatalystHCID 3283Diethyl EtherSolvent

Procedure

225 g (1.09 mol) of dicyclohexylcarbodiimide (DCC) are added in portions, while cooling with ice, to a solution of 160 g (1.095 mol) of tetrahydro-5-oxo-3-thiophenecarboxylic acid, 70 g (2.19 mol) of methanol and 4 g (32.8 mmol) of dimethylaminopyridine (DMAP) in 2.5 litres of diethyl ether. After 4 hours' stirring at room temperature, the dicyclohexylurea is filtered off and the filtrate is extracted with 500 ml of 2N hydrochloric acid and 500 ml of saturated sodium hydrogen carbonate solution, is washed with water and is dried over sodium sulfate. There are obtained 149 g of solid product having a melting point of 33°-35° C.

Workup

  1. filtrationthe dicyclohexylurea is filtered off
  2. extractionthe filtrate is extracted with 500 ml of 2N hydrochloric acid and 500 ml of saturated sodium hydrogen carbonate solution
  3. washis washed with water
  4. dry with materialis dried over sodium sulfate

Sources & evidence

ORD record
ord-763a0ab795d6455bbae084653ef8ca5e
Source dataset
uspto-grants-1998_09
Patent number
US05814629

Reaction notes

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