Ethoxalyl chloride → HCID 54318024, compound

HRID 411119Notes

Reaction equation

HRID 411119 reaction equation
Cl[C:2](=[O:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:9]([C:13]1[CH:19]=[C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:17]=[C:16]([C:24]([CH3:27])([CH3:26])[CH3:25])[C:14]=1[NH2:15])([CH3:12])([CH3:11])[CH3:10]>C(N(CC)CC)C.ClCCl>[CH2:6]([O:5][C:3](=[O:4])[C:2]([NH:15][C:14]1[C:16]([C:24]([CH3:25])([CH3:26])[CH3:27])=[CH:17][C:18]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:19][C:13]=1[C:9]([CH3:12])([CH3:11])[CH3:10])=[O:8])[CH3:7]

Participants

5

Reactant 2

HCID 20884Ethoxalyl chlorideHCID 704022,4,6-Tri-tert-butylaniline

Product 1

HCID 54318024HCID 54318024, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

In a 500 mL round bottom flask, 2,4,6-tri-tert-butylaniline (2.0 g) and 2.6 mL triethylamine were dissolved in dichloromethane (50 mL) and cooled to 0° C. A mixture of ethyl chloroglyoxylate (0.85 mL) and dichloromethane (33 mL) was slowly added via dropping funnel, after which the mixture was stirred at 0° C. for 1 h, and then at 25° C. for 3 h. The resultant mixture was quenched with 100 mL of water. The aqueous layer was extracted with 100 mL of dichloromethane. The combined organic layers were dried over sodium sulfate, filtered, and concentrated under reduced pressure (20 mm Hg). The residue was purified by flash chromatography (silica; hexane/EtOAc; linear gradient). The N-(2,4,6-tri-tert-butylphenyl)oxalamic acid ethyl ester so obtained (201.5 mg) was reacted with excess hydrazine hydrate (81 μL) in 5 mL of EtOH at 50° C. for 14 h. The resultant solid was isolated by filtration and washed with EtOH to obtain compound a38.

Workup

  1. additionwas slowly added
  2. waitat 25° C. for 3 h
  3. customThe resultant mixture was quenched with 100 mL of water
  4. extractionThe aqueous layer was extracted with 100 mL of dichloromethane
  5. dry with materialThe combined organic layers were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure (20 mm Hg)
  8. customThe residue was purified by flash chromatography (silica; hexane/EtOAc; linear gradient)

Sources & evidence

ORD record
ord-95b69124c07347e4990a6401968c35d4
Source dataset
uspto-grants-2003_05
Patent number
US06559091B1

Reaction notes

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