Diethyl bromomalonate → HCID 20144889, compound

HRID 1109603Notes

Reaction equation

HRID 1109603 reaction equation
[S:1]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5](=S)[NH:4][CH2:3][CH2:2]1.Br[CH:13]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:14]([O:16][CH2:17][CH3:18])=[O:15].C(=O)([O-])O.[K+]>C(Cl)Cl>[S:1]1[C:7]2[C:8](=[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:9][S:10][C:6]=2[CH2:5][NH:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 69637Diethyl bromomalonateHCID 516893Potassium BicarbonateHCID 11446993HCID 11446993, compound

Product 1

HCID 20144889HCID 20144889, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

ca) 8.05 g of 3,4-dihydro-thieno[2,3-f][1,4]thiazepine-5(2H)-thione were suspended in 40 ml of methylene chloride and treated under argon with a solution of 7.1 ml of diethyl bromomalonate in 40 ml of methylene chloride. After stirring for 2.5 hours, 50 ml of 10 percent potassium hydrogen carbonate solution were added thereto and the mixture was stirred for 30 minutes. The organic phase was separated and the aqueous phase was extracted twice with methylene chloride. After drying with sodium sulfate, the extract was chromatographed on silica gel, whereby diethyl [3,4-dihydrothieno[2,3-f][1,4]thiazepine-8-(5H)-ylidene]malonate was obtained in the form of slightly yellowish crystals of m.p. 87°-89° (cyclohexane).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. customThe organic phase was separated
  3. extractionthe aqueous phase was extracted twice with methylene chloride
  4. dry with materialAfter drying with sodium sulfate
  5. customthe extract was chromatographed on silica gel

Sources & evidence

ORD record
ord-4bee68bc5f124631bf879b6510d3ad17
Source dataset
uspto-grants-1994_06
Patent number
US05321021

Reaction notes

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