Triethylamine → HCID 14985789, compound

HRID 2261240Notes

Reaction equation

HRID 2261240 reaction equation
C(Cl)(=O)C(Cl)=O.[C:7]1([C:13](=[O:17])[C:14]([OH:16])=O)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[CH2:18]([NH2:21])[C:19]#[CH:20].C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl.O>[O:17]=[C:13]([C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[C:14]([NH:21][CH2:18][C:19]#[CH:20])=[O:16]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 11915Phenylglyoxylic AcidHCID 65578Oxalyl chlorideHCID 239041Propargylamine

Product 1

HCID 14985789HCID 14985789, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Oxalyl chloride (6.1 g, 48 mmol) was added to a solution of phenylglyoxylic acid (6.0 g, 40 mmol) and 3 drops of DMF in dry DCM (50 mL). The reaction mixture was stirred at RT for 3 h then the solvent was removed. The residue was taken up in dry DCM (50 mL) and the solution was cooled to 0° C. A mixture of propargyl amine (2.2 g, 40 mmol) and triethylamine (4.05 g, 40 mmol) was added cautiously over a period of 10 min then the mixture was allowed to warm to RT. Stirring was continued for 2.5 h then water (10 mL) was added. The mixture was washed with 1 M HCl, sat. sodium hydrogencarbonate (aq.), then brine. The organic phase was then dried (Na2SO4) and the solvent was removed. The residue was crystallized from cyclohexane to afford the product as a light brown solid.

Workup

  1. customthe solvent was removed
  2. temperaturethe solution was cooled to 0° C
  3. additionwas added cautiously over a period of 10 min
  4. temperatureto warm to RT
  5. stirringStirring
  6. waitwas continued for 2.5 h
  7. washThe mixture was washed with 1 M HCl, sat. sodium hydrogencarbonate (aq.)
  8. dry with materialThe organic phase was then dried (Na2SO4)
  9. customthe solvent was removed
  10. customThe residue was crystallized from cyclohexane

Sources & evidence

ORD record
ord-0d5d2c2c057f441abe29ecc33f17b126
Source dataset
uspto-grants-2010_12
Patent number
US07846955B2

Reaction notes

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