1,2-Dichloroethane → HCID 21715825, compound

HRID 1387463Notes

Reaction equation

HRID 1387463 reaction equation
C(O[C:4](=[O:14])[C:5]1[CH:10]=[C:9]([O:11][CH2:12][CH3:13])[CH:8]=[N:7][CH:6]=1)C.[OH-].[Na+].Cl.[NH:18]([O:20][CH3:21])[CH3:19].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CN1CCOCC1>CCO.CN(C=O)C>[CH2:12]([O:11][C:9]1[CH:8]=[N:7][CH:6]=[C:5]([CH:10]=1)[C:4]([N:18]([O:20][CH3:21])[CH3:19])=[O:14])[CH3:13]

Participants

10

Reactant 7

HCID 111,2-DichloroethaneHCID 313Hydrochloric Acid2×HCID 79724-MethylmorpholineHCID 14232N,O-DimethylhydroxylamineHCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 20674678HCID 20674678, compound

Product 1

HCID 21715825HCID 21715825, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 16-2 (15 g, 72 mmol) in EtOH (100 mL) was added 1N NaOH (80 ml, 80 mmol). After stirring for 1 h, the solvents were evaporated and the residue was dissolved in 1N HCl (80 ml, 80 mmol) and then concentrated, azeotroped with CH3CN to give the crude acid. The crude acid was suspended in DMF (200 mL) and then treated with HCl.HN(Me)OMe (13.9 g, 144 mmol), EDC (15.1 g, 79.2 mmol), HOBT (9.6 g, 72 mmol) and NMM (60 mL, 576 mmol). The mixture was stirred for 18 hours and then concentrated. The residue was dissolved in ethyl acetate, washed with 10% K2CO3, brine, dried (MgSO4), and concentrated to give amide 16-3 as a brown oil.

Workup

  1. customthe solvents were evaporated
  2. concentrationconcentrated
  3. customazeotroped with CH3CN
  4. customto give the crude acid
  5. stirringThe mixture was stirred for 18 hours
  6. concentrationconcentrated
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 10% K2CO3, brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-e7c2730c86e74b3893af2ee09cef7159
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

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