Ethyl bromopyruvate → HCID 56619518, compound

HRID 621724Notes

Reaction equation

HRID 621724 reaction equation
NC1CCCC(=[O:8])C=1.BrCC(=O)C(OCC)=O.[Br:18][CH2:19][C:20](=[C:26]1[C:31](=O)[CH2:30][CH2:29][CH2:28][C:27]1=[NH:33])[C:21]([O:23][CH2:24][CH3:25])=[O:22]>C(OCC)(=O)C>[Br:18][CH2:19][C:20](=[C:26]1[CH2:31][C:30](=[O:8])[CH2:29][CH2:28][C:27]1=[NH:33])[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Participants

5

Reactant 3

HCID 66144Ethyl bromopyruvateHCID 788923-Aminocyclohex-2-en-1-oneHCID 56623083HCID 56623083, compound

Product 1

HCID 56619518HCID 56619518, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

111.1 g. 1-Aminocyclohex-1-en-3-one (see Arch. Pharm., 294, 763/1961) are added at 30° C., with stirring, to 760 ml. ethyl bromopyruvate. The reaction mixture is then heated to 60° C. for 8 hours. After cooling, the reaction mixture is mixed with 200 ml. ethyl acetate and 1000 ml. diethyl ether and filtered with suction. After washing the solid product with diethyl ether, there are obtained 247 g. (85% of theory) ethyl 3-bromo-2-(2-imino-6-oxocyclohexylidene)-propionate; m.p. 170°-175° C.

Workup

  1. temperatureAfter cooling
  2. additionthe reaction mixture is mixed with 200 ml
  3. filtrationdiethyl ether and filtered with suction
  4. washAfter washing the solid product with diethyl ether, there
  5. customare obtained 247 g

Sources & evidence

ORD record
ord-f7dbb564332249b6942ea366f4c81662
Source dataset
uspto-grants-1989_04
Patent number
US04824965

Reaction notes

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