Phenylacetyl chloride → HCID 21190021, compound

HRID 1781059Notes

Reaction equation

HRID 1781059 reaction equation
[OH:1][C:2]1[C:3]2[C:8]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])=[N:7][C:6](=[O:16])[C:5](=[O:17])[N:4]=2.C(N(CC)CC)C.[C:25]1([CH2:31][C:32](Cl)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>C(Cl)Cl>[C:25]1([CH2:31][C:32]([O:1][C:2]2[C:3]3[C:8]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=2[O:12][CH3:13])=[N:7][C:6](=[O:16])[C:5](=[O:17])[N:4]=3)=[O:33])[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 136092328HCID 136092328, compound

Product 1

HCID 21190021HCID 21190021, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-hydroxy-6,7-dimethoxy-2,3-quinoxalinedione (48) (50 mg, 0.22 mmol) in 3 mL of methylene dichloride was added 0.14 mL of triethylamine and phenylacetyl chloride (77.5 mg, 0.5 mmol, Aldrich) at 0° C. The resulting mixture was stirred at room temperature for 12 hr. The reaction mixture was then poured into ice-water (5 g). A white solid precipitated and was collected by suction filtration, washed with water (3×5 mL) and ethyl acetate (3×2 mL), and dried in vacuo, giving 60 mg (77%) of the product as a white solid; mp 298°-300° C.; 1H NMR (DMSO-d6, 300 MHz) δ3.405 (s, 3H), 3.728 (s, 3H), 4.024 (s, 2H), 6.653 (s, 1H), 7.359 (m, 5H), 11.773 (s, 1H), 11.846 (s, 1H). EIMS m/e 356 (25, M+), 238 (100). (HPLC 100%).

Workup

  1. customA white solid precipitated
  2. filtrationwas collected by suction filtration
  3. washwashed with water (3×5 mL) and ethyl acetate (3×2 mL)
  4. customdried in vacuo

Sources & evidence

ORD record
ord-f001a64fe8f24ef6a5090cd755cd65c4
Source dataset
uspto-grants-1997_05
Patent number
US05631373

Reaction notes

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