N-(4-chlorophenyl)benzene-1,2-diamine → HCID 70979050, compound

HRID 1485379Notes

Reaction equation

HRID 1485379 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2[C:10]([NH2:15])=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:4][CH:3]=1.[CH3:16][C:17]([CH3:24])([C:21](Cl)=[O:22])[C:18](Cl)=[O:19]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:18](=[O:19])[C:17]([CH3:24])([CH3:16])[C:21](=[O:22])[NH:15][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]2=3)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 522323N-(4-chlorophenyl)benzene-1,2-diamineHCID 4523180Dimethylmalonyl Dichloride

Product 1

HCID 70979050HCID 70979050, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred refluxing solution of N1-(4-chlorophenyl)benzene-1,2-diamine (200 mg, 0.92 mmol) in toluene (20 mL) was added drop-wise a solution of 2,2-dimethylmalonyl dichloride (155 mg, 0.92 mmol). Then the mixture was refluxed for 1 h. The solvent was removed in vacuum, stirred with water (20 mL), extracted with DCM (20 mL×3). The combined organic layer was dried over Na2SO4. The mixture was concentrated in vacuum and the residue was purified by column chromatography (silica-gel, DCM: methanol=40:1) to give 1-(4-chlorophenyl)-3,3-dimethyl-1H-benzo[b][1,4]diazepine-2,4(3H,5H)-dione as a yellow solid (167.5 mg, 58%). LRMS (M+H+) m/z: calcd 314.08. found 314.

Workup

  1. temperatureThen the mixture was refluxed for 1 h
  2. customThe solvent was removed in vacuum
  3. extractionextracted with DCM (20 mL×3)
  4. dry with materialThe combined organic layer was dried over Na2SO4
  5. concentrationThe mixture was concentrated in vacuum
  6. customthe residue was purified by column chromatography (silica-gel, DCM: methanol=40:1)

Sources & evidence

ORD record
ord-6e8f9fc3236a405c9ded9665da781c2d
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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