Diethyl Ether → HCID 178470405, compound

HRID 265202Notes

Reaction equation

HRID 265202 reaction equation
CI.[Mg].C(C1NC(C(OCC)=O)=[C:9]([C:11](OCC)=[S:12])N=1)C.[OH:21][C:22]([C:25]1[N:26]=[C:27](C)[NH:28][C:29]=1[C:30]([O:32][CH2:33][CH3:34])=S)([CH3:24])[CH3:23].C([O:38]CC)C>C(Cl)Cl>[CH2:11]([S:12][C:27]1[NH:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:38])=[C:25]([C:22]([OH:21])([CH3:24])[CH3:23])[N:26]=1)[CH3:9]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 5462224MagnesiumHCID 178470391HCID 178470391, compoundHCID 178473691HCID 178473691, compound

Product 1

HCID 178470405HCID 178470405, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.20 g of methyl iodide were added dropwise to a mixture of 714 mg of magnesium in 30 ml of diethyl ether, under a nitrogen atmosphere, and the resulting solution was heated under reflux, whilst stirring, for 30 minutes. At the end of this time, a solution of 2.00 g of diethyl 2-ethylthioimidazole-4,5-dicarboxylate [prepared as described in step (i) above] in 20 ml of methylene chloride was added dropwise to the reaction solution, and the mixture was treated in a similar manner to that described in Preparation 49(ii). The resulting crystalline residue was washed with a mixture of hexane and diisopropyl ether, to give 1.32 g of title compound, melting at 82°-85° C.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureunder reflux
  3. additionthe mixture was treated in a similar manner to that
  4. washThe resulting crystalline residue was washed with a mixture of hexane and diisopropyl ether

Sources & evidence

ORD record
ord-f93888b2e6ab40cfb2f53fe3531f0c79
Source dataset
uspto-grants-1997_07
Patent number
US05646171

Reaction notes

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