Water → HCID 12846663, compound

HRID 2417935Notes

Reaction equation

HRID 2417935 reaction equation
N12CCCC1=NCCC2.Br[CH:11]([CH:22](Br)[C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[C:12](=[O:21])[CH2:13][C:14](=[O:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16].O>CS(C)=O>[CH3:30][O:29][C:26]1[CH:27]=[CH:28][C:23]([C:22]2[O:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][C:12](=[O:21])[CH:11]=2)=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 763491,5-Diazabicyclo(4.3.0)non-5-eneHCID 15578367HCID 15578367, compound

Product 1

HCID 12846663HCID 12846663, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1,5-Diazabicyclo[4.3.0]non-5-ene (3.2 g) was added dropwise to a stirred solution of ethyl 5,6-dibromo-2,4-dioxo-6-(4-methoxyphenyl)-hexanoate (5.6 g) in dimethylsulphoxide (30 ml) maintained at a temperature of 15°-20° C. After 30 minutes at room temperature, water (50 ml) and petroleum ether 40°-60° C. (20 ml) were added with cooling. The yellow solid which precipitated was filtered off and recrystallised from ethanol-water. A second recrystallisation from ethyl acetatepetroleum ether 60°-80° C. yielded the title product as yellow needles (mp 131°-133° C. with sublimation).

Workup

  1. temperaturemaintained at a temperature of 15°-20° C
  2. temperaturewith cooling
  3. customThe yellow solid which precipitated
  4. filtrationwas filtered off
  5. customrecrystallised from ethanol-water
  6. customA second recrystallisation from ethyl acetatepetroleum ether 60°-80° C.

Sources & evidence

ORD record
ord-64b6e1b6ddc04410b529bca3734203d1
Source dataset
uspto-grants-1984_09
Patent number
US04471129

Reaction notes

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