Hydrochloric Acid → HCID 359722, compound

HRID 1690850Notes

Reaction equation

HRID 1690850 reaction equation
C1CCN2C(=NCCC2)CC1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH2:19][C:20]#[N:21])=[CH:15][CH:14]=1.[CH2:22]([O:24][C:25](=[O:31])[C:26](OCC)=[O:27])[CH3:23].Cl>C(#N)C.C(OCC)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]([C:20]#[N:21])[C:26](=[O:27])[C:25]([O:24][CH2:22][CH3:23])=[O:31])=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7268Diethyl OxalateHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2415824-Chlorobenzyl cyanide

Product 1

HCID 359722HCID 359722, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 542 μL (3.63 mmol) sample of DBU was added to a solution of 500 mg (3.30 mmol) of 4-chlorophenylacetonitrile and 493 μL (3.63 mmol) of diethyloxalate in 1.6 mL of acetonitrile. After ca. 10 min, the mixture was diluted with ethyl acetate and acidified with dilute HCl. The organic phase was washed with three portions of water, dried and stripped to an oily solid. Trituration with hexane/butyl chloride yielded 414 mg, m. p. 135-136° C. A second crop of 35 mg gave a total yield of 54% of ethyl 3-(4-chlorophenyl)-3-cyano-2-oxopropanoate.

Workup

  1. washThe organic phase was washed with three portions of water
  2. customdried
  3. customTrituration with hexane/butyl chloride yielded 414 mg, m. p. 135-136° C

Sources & evidence

ORD record
ord-e2e22ebb436042e783128f70d5e1920a
Source dataset
uspto-grants-2012_04
Patent number
US08153688B2

Reaction notes

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