1,2-Dichloroethane → HCID 70972224, compound

HRID 2409914Notes

Reaction equation

HRID 2409914 reaction equation
[O:1]1[C:5]([C:6]2[CH:7]=[C:8]([CH:12]=[CH:13][CH:14]=2)[C:9](O)=[O:10])=[CH:4][N:3]=[CH:2]1.Cl.CN.C(Cl)CCl.C1C=[N:26][C:25]2N(O)N=NC=2C=1.CCN(C(C)C)C(C)C>CCOC(C)=O.CO.CN(C=O)C>[CH3:25][NH:26][C:9](=[O:10])[C:8]1[CH:12]=[CH:13][CH:14]=[C:6]([C:5]2[O:1][CH:2]=[N:3][CH:4]=2)[CH:7]=1

Participants

9

Reactant 5

HCID 111,2-DichloroethaneHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 6364545Methylamine hydrochlorideHCID 71278133-(1,3-oxazol-5-yl)benzoic Acid

Product 1

HCID 70972224HCID 70972224, compoundYield 48%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

DMF (15.9 mL) was added to a round bottom flask containing 3-(oxazol-5-yl)benzoic acid (0.99 gm, 5.23 mmol), methylamine hydrochloride (0.39 gm, 5.76 mmol), EDC (1.10 gm, 5.76 mmol), and HOAt (0.78 gm, 5.76 mmol). DIPEA (2.29 mL, 13.08 mmol) was then added. The reaction mixture was stirred at rt overnight. After 24 h the mixture was partitioned between EtOAc and water. The organic phase was isolated, washed with saturated aqueous NaCl, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography eluting with a gradient of 0-100% EtOAc/Hexanes then 15% MeOH in EtOAc to give the product, N-methyl-3-(oxazol-5-yl)benzamide, (0.50 gm, 2.49 mmol, 48% yield) as a white solid. Anal. Calcd. for C11H10N2O2 m/z 202.1, found: 203.1 (M+H)+.

Workup

  1. customAfter 24 h the mixture was partitioned between EtOAc and water
  2. customThe organic phase was isolated
  3. washwashed with saturated aqueous NaCl
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified
  8. washeluting with a gradient of 0-100% EtOAc/Hexanes

Sources & evidence

ORD record
ord-dfe440ed1c464e049ded24fa8671699f
Source dataset
uspto-grants-2014_08
Patent number
US08815909B2

Reaction notes

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