Phenylglyoxylic Acid → HCID 15152037, compound

HRID 1770085Notes

Reaction equation

HRID 1770085 reaction equation
[C:1]([C:9]([OH:11])=[O:10])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:12][CH:13](O)[C:14]#[CH:15].Cl.C(N=C=NCCCN(C)C)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[I:12][C:13]#[C:14][CH2:15][O:10][C:9]([C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11]

Participants

6

Reactant 3

HCID 11915Phenylglyoxylic AcidHCID 602749Iodopropargyl alcoholHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 15152037HCID 15152037, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a cold, stirred solution of benzoyl formic acid (1.5 g, 0.01 mole) in methylene chloride (75 mL) at 4° C. were added iodopropargyl alcohol (1.9 g, 0.0105 mole) followed by 4-dimethylaminopyridine (0.122 g, 0.001 mole) and ethyl-(3-dimethylaminopropyl)carbodiimide hydrochloride (2 g, 0.0104 mole). After stirring at 0° to 10° C. for one hour, the reaction mixture was diluted with methylene chloride (100 mL) and was washed with water (3×50 mL) and brine. The organic layer was dried over sodium sulfate, filtered, and concentrated to a residue. The residue was triturated with hexane and the product, a pale yellow solid, was collected by suction-filtration yielding 1.75 g (60%), mp=48°-50° C. An nmr spectrum showed the desired compound.

Workup

  1. washwas washed with water (3×50 mL) and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a residue
  5. customThe residue was triturated with hexane
  6. filtrationthe product, a pale yellow solid, was collected by suction-filtration
  7. customyielding 1.75 g (60%), mp=48°-50° C

Sources & evidence

ORD record
ord-b935b8276af04cd1a30984664edeb204
Source dataset
uspto-grants-1995_01
Patent number
US05385902

Reaction notes

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