HCID 23362032, compound → HCID 68762744, compound

HRID 1628577Notes

Reaction equation

HRID 1628577 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](N)[C:3]=1[NH:9][CH2:10][CH2:11][OH:12].Cl.[Cl:14][C:15]1[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=1[CH:22]([OH:27])[C:23](=[NH:26])OC>C(O)C.C(=O)([O-])O.[Na+]>[NH2:1][C:2]1[C:3]2[N:9]([CH2:10][CH2:11][OH:12])[C:23]([CH:22]([C:16]3[CH:17]=[CH:18][C:19]([Cl:21])=[CH:20][C:15]=3[Cl:14])[OH:27])=[N:26][C:4]=2[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 23362032HCID 23362032, compoundHCID 68736952HCID 68736952, compound

Product 1

HCID 68762744HCID 68762744, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 2-[(2,6-diaminophenyl)amino]ethanol (3.63 g, 21.7 mmol) in ethanol (43 mL) was added methyl 2-(2,4-dichlorophenyl)-2-hydroxyethanimidoate hydrochloride (7.04 g, 26.0 mmol) at room temperature. After 12 h, the reaction mixture was diluted with aqueous sodium hydrogen carbonate. The resultant mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with ethyl acetate to give the title compound as an orange amorphous solid (7.58 g, 21.5 mmol, 99%).

Workup

  1. extractionThe resultant mixture was extracted with ethyl acetate
  2. washThe combined organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel eluting with ethyl acetate

Sources & evidence

ORD record
ord-c9c5ba60a18b406a8f64abb811614903
Source dataset
uspto-grants-2014_07
Patent number
US08785460B2

Reaction notes

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