2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 14460145, compound

HRID 1590077Notes

Reaction equation

HRID 1590077 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([CH:33]([CH3:35])[CH3:34])[NH:25][CH:24]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[N:23]=2)=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[F:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[C:26]([CH:33]([CH3:34])[CH3:35])[N:25]=[C:24]([C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)[N:23]=2)=[CH:20][CH:21]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 19769502HCID 19769502, compound

Product 1

HCID 14460145HCID 14460145, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

2,3-Dichloro-5,6-dicyanobenzoquinone (DDQ) (7.69 gm, 34 mmol) was added to a solution of 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-ethoxycarbonyl-1,2-dihydropyrimidine obtained in step (i) above (10.200 gm, 28 mmol) in toluene (200 ml). The red solution was then heated at 50° C. for 3 hours. The solution was cooled to room temperature, then passed through a silica gel plug which was washed with 10% EtOAc in hexane. The filtrate was concentrated to give an amber oil. The oil was purified by flash chromatography on Merck silica gel in 15% EtOAc in hexane. Fractions containing the desired product were pooled and concentrated to give a clear oil which solidified to afford the title compound as a white, crystalline solid (8.800 gm, 87%) (mp 97°-99° C.).

Workup

  1. temperatureThe solution was cooled to room temperature
  2. washwas washed with 10% EtOAc in hexane
  3. concentrationThe filtrate was concentrated
  4. customto give an amber oil
  5. customThe oil was purified by flash chromatography on Merck silica gel in 15% EtOAc in hexane
  6. additionFractions containing the desired product
  7. concentrationconcentrated
  8. customto give a clear oil which

Sources & evidence

ORD record
ord-b25d6142daca4a6793e8c988956e5394
Source dataset
uspto-grants-1993_04
Patent number
US05202327

Reaction notes

Loading…