Hydrochloric Acid → HCID 22013068, compound

HRID 378703Notes

Reaction equation

HRID 378703 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].CC(C)([O-])C.[K+].[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22]Br)[CH3:19].Cl>CS(C)=O>[CH2:18]([O:20][CH:21]([O:24][CH2:25][CH3:26])[CH2:22][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7054IsatinHCID 74852Ethane, 2-bromo-1,1-diethoxy-HCID 23665647Potassium tert-butoxide

Product 1

HCID 22013068HCID 22013068, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

A solution of 31.8 g of isatin in 300 ml of dry dimethyl sulfoxide was added dropwise to a suspension of 25.4 g of potassium t-butoxide in 200 ml of dry dimethyl sulfoxide at 10° C. in a nitrogen stream. After stirring the mixture at that temperature for 30 minutes, 39 ml of bromoacetaldehyde diethyl acetal was added thereto, followed by stirring at 70° C. for 6 hours. The reaction mixture was poured into dilute hydrochloric acid and extracted with ethyl ether. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (chloroform/ethyl acetate=20/1) to give 31.4 g (55%) of the title compound as a red powder.

Workup

  1. stirringby stirring at 70° C. for 6 hours
  2. extractionextracted with ethyl ether
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel column chromatography (chloroform/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-78314d8cbff04c4cb6805b972ae30c5c
Source dataset
uspto-grants-2000_02
Patent number
US06031111

Reaction notes

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