2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → 3-[(8-Phenylthieno[2,3-h]quinazolin-2-yl)amino]benzenesulfonamide

HRID 643733Notes

Reaction equation

HRID 643733 reaction equation
[C:1]1([C:7]2[S:30][C:10]3[CH2:11][CH2:12][C:13]4[CH:14]=[N:15][C:16]([NH:19][C:20]5[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=5)=[N:17][C:18]=4[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCOCC1>[C:1]1([C:7]2[S:30][C:10]3=[CH:11][CH:12]=[C:13]4[C:18]([N:17]=[C:16]([NH:19][C:20]5[CH:21]=[C:22]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:23]=[CH:24][CH:25]=5)[N:15]=[CH:14]4)=[C:9]3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 11750889HCID 11750889, compound

Product 1

HCID 532456993-[(8-Phenylthieno[2,3-h]quinazolin-2-yl)amino]benzenesulfonamideYield 39%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a dark solution of 3-(8-Phenyl-5,6-dihydro-thieno[2,3-h]quinazolin-2-ylamino)-benzenesulfonamide (130 mg, 0.30 mmol) in anhydrous 1,4-dioxane (7 mL) was added DDQ (75 mg, 0.33 mmol) and the mixture was refluxed under nitrogen for 2-3 hours. The reaction mixture was concentrated in vacuo and the resulting crude residue was triturated in a mixture of 2M NaOH (25 mL) and DCM (25 mL). The resulting solid was filtered and washed with DCM and water to afford 50 mg (39% yield) of the title compound as a pale yellow/green powder. MS (ES+) 433, (ES−) 431. δH (d6 DMSO) 7.39 (2H, br s), 7.41 (1H, m), 7.51 (4H, br m), 7.72 (1H, d), 7.83 (1H, d), 7.96 (3H, m), 8.68 (1H, s), 9.40 (1H, s), 9.61 (1H, br s) and 10.41 (1H, s).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 2-3 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe resulting crude residue was triturated in a mixture of 2M NaOH (25 mL) and DCM (25 mL)
  4. filtrationThe resulting solid was filtered
  5. washwashed with DCM and water

Sources & evidence

ORD record
ord-ff6f04bc237f4a308d0c21c4c3ba6484
Source dataset
uspto-grants-2010_04
Patent number
US07700609B2

Reaction notes

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