2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 57982550, compound

HRID 1868449Notes

Reaction equation

HRID 1868449 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[N:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])[N:16]=[C:12]3[NH:11][C:10]([CH3:25])=[C:9]2[C:26]#[N:27])=[CH:4][C:3]=1[F:28].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]3[CH:14]=[C:15]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[O:23][CH3:24])[N:16]=[C:12]3[N:11]=[C:10]([CH3:25])[C:9]=2[C:26]#[N:27])=[CH:4][C:3]=1[F:28]

Participants

4

Reactant 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 57982559HCID 57982559, compound

Product 1

HCID 57982550HCID 57982550, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred suspension of 5-(4-chloro-3-fluorophenyl)-2-(2-methoxyphenyl)-7-methyl-5,8-dihydroimidazo[1,2-a]pyrimidine-6-carbonitrile (180 mg, 0.46 mmol) in CH2Cl2 (5 mL) was added 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (103 mg, 0.46 mmol) in one portion. The reaction was kept at ambient temperature for 2.5 h, diluted with CH2Cl2 and washed with satd aq NaHCO3 (5×). The organic layer was washed again with brine, dried (Na2SO4) and concentrated under reduced pressure to afford 5-(4-chloro-3-fluorophenyl)-2-(2-methoxyphenyl)-7-methylimidazo[1,2-a]pyrimidine-6-carbonitrile (168 mg, 94%) as a light orange solid.

Workup

  1. washwashed with satd aq NaHCO3 (5×)
  2. washThe organic layer was washed again with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d19a9f3f3afc4ab2b0a7cc0d3e0c81fb
Source dataset
uspto-grants-2009_12
Patent number
US07635699B2

Reaction notes

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