Water → HCID 86583565, compound

HRID 1016793Notes

Reaction equation

HRID 1016793 reaction equation
ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl.[C:15]([C:17]1[CH:22]=[CH:21][C:20]([NH:23][CH:24]([C:30]2[CH:35]=[C:34]([CH:36]=O)[CH:33]=[C:32]([O:38][CH2:39][CH3:40])[CH:31]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[CH:19][CH:18]=1)#[N:16].[C:41]1([NH2:48])[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[NH2:47].O>C(#N)C>[NH:47]1[C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=2[N:48]=[C:36]1[C:34]1[CH:35]=[C:30]([CH:24]([NH:23][C:20]2[CH:19]=[CH:18][C:17]([C:15]#[N:16])=[CH:22][CH:21]=2)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:31]=[C:32]([O:38][CH2:39][CH3:40])[CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7243O-PhenylenediamineHCID 86583566HCID 86583566, compound

Product 1

HCID 86583565HCID 86583565, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in acetonitrile (1.5 ml) was added dropwise very slowly (2 h.) to a solution of the ethyl (RS)-(4-cyano-phenylamino)-(3-ethoxy-5-formyl-phenyl)-acetate (460 mg, 1.305 mmol) obtained in Example 244.1 and 1,2-phenylenediamine in acetonitrile (2 ml). The reaction mixture was stirred for 4 h. at room temperature. Water/saturated Na2CO3 solution (1:1) was added and the mixture was extracted with CH2Cl2. The organic phase was washed with H2O, dried, filtered and concentrated. The residue was purified by chromatography (SiO2, hexane/EtOAc 3:2). There were obtained 173 mg (30%) of ethyl (RS)-[3-(1H-benzoimidazol-2-yl)-5-ethoxy-phenyl]-(4-cyano-phenylamino)-acetate as a colorless solid; MS: 441 ([M+H]+).

Workup

  1. extractionthe mixture was extracted with CH2Cl2
  2. washThe organic phase was washed with H2O
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (SiO2, hexane/EtOAc 3:2)

Sources & evidence

ORD record
ord-3aa1412e4a6a4da3995edb95b67f46ff
Source dataset
uspto-grants-2002_11
Patent number
US06476264B2

Reaction notes

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