2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 22648049, compound

HRID 394084Notes

Reaction equation

HRID 394084 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH2:12][NH:11][C:10]1=[O:29].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[N:9]1[C:18]2[C:13](=[C:14]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=2)[CH:12]=[N:11][C:10]1=[O:29]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 22648176HCID 22648176, compound2×

Product 1

HCID 22648049HCID 22648049, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a solution of 1-(2,6-dichlorophenyl)-5-(2-chlorofluorophenyl)-7-methoxy-3,4-dihydro-2(1H)-quinazolinone (112 mg, 0.248 mmol) (INTERMEDIATE 30) in 1,4-dioxane (5 mL) at 65° C. under an argon atmosphere was added a solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (115 mg, 0.51 mmol) in 1,4-dioxane (2.5 mL). After 2 h the solution was cooled to RT and partitioned between NaHCO3 and EtOAc. The phases were separated and the organic phase washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by silica gel chromatography using 3 to 5% acetone in DCM as the eluent to give 1-(2,6-dichlorophenyl)-5-(2-chloro-4-fluorophenyl)-7-(methoxy)-2(1H)-quinazolinone. 1H NMR(CDCl3, 500 MHz): δ 3.70 (s, 3H), 5.94 (d, 1H, J=2.1 Hz), 6.74 (d, 1H, J=2.1 Hz), 7.18 (app dt, 1H, J=8.1, 2.5 Hz), 7.35 (m, 1H), 7.42 (m, 1H), 7.47 (t, 1H, J=8.2 Hz), 7.56-7.60 (m, 2H). MS(ES) 449 (M+H); LC 1: 3.40 min.

Workup

  1. custompartitioned between NaHCO3 and EtOAc
  2. customThe phases were separated
  3. washthe organic phase washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-3fcecf198dd34659acd00060a24b8227
Source dataset
uspto-grants-2004_10
Patent number
US06809199B2

Reaction notes

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