2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57839063, compound

HRID 732960Notes

Reaction equation

HRID 732960 reaction equation
[CH2:1]([S:8][C:9]1[NH:10][C:11]([CH3:27])=[C:12]([C:23]([O:25][CH3:26])=[O:24])[CH:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[N:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>C(Cl)Cl.C1CCCCC1.CCOC(C)=O>[CH2:1]([S:8][C:9]1[N:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=2[Cl:22])[C:12]([C:23]([O:25][CH3:26])=[O:24])=[C:11]([CH3:27])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57839038HCID 57839038, compound

Product 1

HCID 57839063HCID 57839063, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21867204Cyclohexane ethylacetateSolvent

Procedure

The crude methyl 2-(benzylthio)-4-(2,4-dichlorophenyl)-6-methyl-1,4-dihydropyrimidine-5-carboxylate (0.22 mmol) from Step 1 was dissolved in CH2Cl2 (2 mL) and DDQ (50 mg, 0.22 mmol) was added. After 1 hr, The reaction was diluted with cyclohexane/EtOAc solution (4:1, 10 mL) and the organic layer was extracted with saturated NaHCO3 solution (2×6 mL), brine (5 mL). The organic layer dried (MgSO4), filtered and concentrated under reduced pressure to give methyl 2-(benzylthio)-4-(2,4-dichlorophenyl)-6-methylpyrimidine-5-carboxylate. The crude reaction product (>95% purity) was moved onto next step without further purification.

Workup

  1. extractionthe organic layer was extracted with saturated NaHCO3 solution (2×6 mL), brine (5 mL)
  2. dry with materialThe organic layer dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-70cb1fbbc118420a83a9132ab05a1174
Source dataset
uspto-grants-2009_09
Patent number
US07589088B2

Reaction notes

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