2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 21109098, compound

HRID 1766090Notes

Reaction equation

HRID 1766090 reaction equation
[NH2:1][C:2]1[C:3]2[C:4]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=3)=[N:5][C:6]([S:17][CH3:18])=[N:7][C:8]=2[CH2:9][CH2:10][C:11]=1[C:12]([O:14][CH2:15][CH3:16])=[O:13].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.C1(C)C=CC=CC=1>[NH2:1][C:2]1[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([N+:25]([O-:27])=[O:26])[CH:20]=1)=[N:5][C:6]([S:17][CH3:18])=[N:7]2

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 21109095HCID 21109095, compound

Product 1

HCID 21109098HCID 21109098, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of crude ethyl 5-amino-2-methylthio-4-(3-nitro-phenyl)-7,8-dihydro-quinazoline-6-carboxylate (example 27d, 1.19 g) in CH2Cl2 (31 ml) was cooled to 0° C. A solution of DDQ (1.14 g) in toluene (31 ml) was added dropwise, the ice-bath removed and the solution was stirred for an additional 30 min at room temperature. The mixture was diluted with CH2Cl2 (ca 100 ml) and washed with a saturated aqueous solution of NaHCO3 (3×100 ml) and brine (2×50 ml). The combined aqueous layers were back-extracted with CH2Cl2. The combined organic layers were dried (MgSO4) and concentrated under reduced pressure. The title compound was purified by chromatography on silica gel using hept/EtOAc=9/1 to 3/2 (v/v) as eluent.

Workup

  1. customthe ice-bath removed
  2. additionThe mixture was diluted with CH2Cl2 (ca 100 ml)
  3. washwashed with a saturated aqueous solution of NaHCO3 (3×100 ml) and brine (2×50 ml)
  4. extractionThe combined aqueous layers were back-extracted with CH2Cl2
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. concentrationconcentrated under reduced pressure
  7. customThe title compound was purified by chromatography on silica gel using hept/EtOAc=9/1 to 3/2 (v/v) as eluent

Sources & evidence

ORD record
ord-4dc1b07d8e184b6aa9315d288f1d7b52
Source dataset
uspto-grants-2007_06
Patent number
US07229990B2

Reaction notes

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