Diethyl Oxalate → 6-Chloro-1-cyclohexyl-2,3(1H,4H)-quinoxalinedione

HRID 1457556Notes

Reaction equation

HRID 1457556 reaction equation
[NH2:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[NH:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1.[C:16](OCC)(=[O:22])[C:17](OCC)=[O:18]>>[Cl:15][C:13]1[CH:14]=[C:2]2[C:3](=[CH:11][CH:12]=1)[N:4]([CH:5]1[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10]1)[C:17](=[O:18])[C:16](=[O:22])[NH:1]2

Participants

3

Reactant 2

HCID 7268Diethyl OxalateHCID 220971504-Chloro-N1-cyclohexylbenzene-1,2-diamine

Product 1

HCID 220971926-Chloro-1-cyclohexyl-2,3(1H,4H)-quinoxalinedioneYield 63%

Procedure

34.5 g (0.15 mol) of 2-amino-4-chloro-N-cyclohexylaniline were refluxed in 500 ml of diethyl oxalate for 4 h. After cooling, the precipitate was filtered off with suction, washed with n-pentane and dried. 26.8 g (63%) of the product were obtained. Melting point 265°-266° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off with suction
  3. washwashed with n-pentane
  4. customdried

Sources & evidence

ORD record
ord-66c42e9cbb084bac973b5caa73c0a32e
Source dataset
uspto-grants-1998_12
Patent number
US05849743

Reaction notes

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