1,2-Dichloroethane → HCID 12206142, compound

HRID 1485480Notes

Reaction equation

HRID 1485480 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([CH3:15])([CH3:14])[CH2:10][C:11](O)=[O:12].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.CN(C=O)C>O>[CH3:14][C:9]1([CH3:15])[CH2:10][C:11](=[O:12])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[NH:8]1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6228DimethylformamideHCID 757711-HydroxybenzotriazoleHCID 86718510HCID 86718510, compound

Product 1

HCID 12206142HCID 12206142, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

An round bottomed flask was charged with crude 3-(2-aminophenylamino)-3-methylbutanoic acid (2.19 g, 10.52 mmol), HOBT (1.932 g, 12.62 mmol), EDC (2.419 g, 12.62 mmol), and a stirbar. DMF (20 mL, 0.5 M) was added, and the solution was stirred at rt overnight. The solution was diluted with water, extracted three times with methylene chloride, dried with sodium sulfate, concentrated with celite, and purified by silica gel chromatography (eluting with hexanes/ethyl acetate/1% isopropanol) to yield 4,4-dimethyl-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one as a yellow amorphous solid (0.697 g, 3.66 mmol, 35%).

Workup

  1. extractionextracted three times with methylene chloride
  2. dry with materialdried with sodium sulfate
  3. concentrationconcentrated with celite
  4. custompurified by silica gel chromatography (eluting with hexanes/ethyl acetate/1% isopropanol)

Sources & evidence

ORD record
ord-aa159ffbd86e4d0fadf97d0c96666c68
Source dataset
uspto-grants-2016_08
Patent number
US09422292B2

Reaction notes

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