Dichloromethane → 1-Cyclopropyl-1,4-dihydroquinoxaline-2,3-dione

HRID 1966977Notes

Reaction equation

HRID 1966977 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[N:7](O)[C:6](=[O:15])[C:5]2=[O:16])[CH2:3][CH2:2]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.ClCCl>CN(C)C=O>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6](=[O:15])[C:5]2=[O:16])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 673201301-Cyclopropyl-4-hydroxy-1,4-dihydro-quinoxaline-2,3-dione

Product 1

HCID 212796951-Cyclopropyl-1,4-dihydroquinoxaline-2,3-dioneYield 84.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

To a solution of 1-cyclopropyl-4-hydroxy-1,4-dihydro-quinoxaline-2,3-dione (31.0 g, 0.14 mol, 1.0 equiv) in N,N-dimethylformamide (250 mL) was added triphenylphosphine (55.9 g, 0.21 mol, 1.5 equiv; [CAS RN 603-35-0]) and the reaction mixture stirred at 135° C. for 4 hours. The reaction mixture was cooled down to 0° C. and dichloromethane (400 mL) was added. The suspension was stirred for 30 min., filtered and washed with dichloromethane (200 mL) providing 23.8 g (83%) of the title compound as a white solid. MS (ISN): m/z=203.1 [M+H]+.

Workup

  1. temperatureThe reaction mixture was cooled down to 0° C.
  2. stirringThe suspension was stirred for 30 min.
  3. filtrationfiltered
  4. washwashed with dichloromethane (200 mL)

Sources & evidence

ORD record
ord-96300f9357764f4bb61787caf82b4f5a
Source dataset
uspto-grants-2013_04
Patent number
US08420647B2

Reaction notes

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