HCID 13730770, compound → HCID 13730765, compound

HRID 1650089Notes

Reaction equation

HRID 1650089 reaction equation
[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.[C:12]([C:14]([N:19]1[C:23](=[O:24])[CH:22]=[C:21]([NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[CH2:33][OH:34])[C:20]1=[O:35])([CH3:18])[CH:15]([CH3:17])[CH3:16])#[N:13]>C(Cl)Cl.CCOCC>[C:12]([C:14]([N:19]1[C:23](=[O:24])[CH:22]=[C:21]([NH:25][C:26]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=2[CH:33]=[O:34])[C:20]1=[O:35])([CH3:18])[CH:15]([CH3:16])[CH3:17])#[N:13]

Participants

5

Reactant 2

HCID 13730770HCID 13730770, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 13730765HCID 13730765, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

Pyridinium chlorochromate (4.4 g, 0.0204 mol) in methylene dichloride (20 ml) is added rapidly to a methylene chloride (20 ml) solution of N-(1-cyano-1,2-dimethylpropyl)-2-(5-chloro-2-hydroxymethylanilino)maleimide (4.75 g, 0.0136 mol). After 2 hours the dark reaction mixture is diluted with ether (20 ml) and a yellow precipitate is formed and is filtered off. This solid is redissolved in ethyl acetate:methylene chloride (1:1) and is passed through a silica gel column to give a yellow solid 4.31 g, (92%) with mp 80° C. (dec.).

Workup

  1. customAfter 2 hours the dark reaction mixture
  2. customa yellow precipitate is formed
  3. filtrationis filtered off
  4. dissolutionThis solid is redissolved in ethyl acetate:methylene chloride (1:1)

Sources & evidence

ORD record
ord-64dbdbdf43fd41ab9c3d53faf43d4140
Source dataset
uspto-grants-1990_05
Patent number
US04923504

Reaction notes

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