Ethyl Acetate → HCID 117699096, compound

HRID 1049721Notes

Reaction equation

HRID 1049721 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[CH:12][CH:11]=1.[C:24](Cl)(=[O:29])[CH2:25][C:26](Cl)=[O:27].C(=O)([O-])O.[Na+].C(OCC)(=O)C>C1COCC1>[C:19]([O:18][C:17]([NH:16][C:13]1[CH:14]=[CH:15][C:10]([N:9]2[C:3]3[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=3[NH:1][C:26](=[O:27])[CH2:25][C:24]2=[O:29])=[CH:11][CH:12]=1)=[O:23])([CH3:20])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 74269Propanedioyl dichlorideHCID 516892Sodium BicarbonateHCID 131736040HCID 131736040, compound

Product 1

HCID 117699096HCID 117699096, compoundYield 33.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

tert-Butyl 4-(2-amino-3-methylphenylamino)phenylcarbamate (294 mg, 0.938 m mmol) was dissolved in THF (30 mL), and then the solution was added dropwise with malonyl chloride (91 μL, 0.938 mmol) under ice cooling. After the disappearance of the starting materials was confirmed, the reaction mixture was added with aqueous sodium hydrogencarbonate, and ethyl acetate, and the organic layer was separated. The organic layer was washed with brine and water, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=100/1) to obtain the title compound (119 mg, yield 33%).

Workup

  1. customthe organic layer was separated
  2. washThe organic layer was washed with brine and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (chloroform to chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-50222b3ce8ed4a81a8de35deac5e6edd
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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