Water → 2,3-Dihydro-1,4-benzodioxine-6-carboxamide

HRID 1747849Notes

Reaction equation

HRID 1747849 reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([OH:13])=O)[CH:9]=[CH:10][C:2]1=2.C1C=CC2N(O)N=[N:20]C=2C=1.N.CCN=C=NCCCN(C)C.Cl.O>CN(C=O)C>[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([C:11]([NH2:20])=[O:13])[CH:9]=[CH:10][C:2]1=2

Participants

6

Reactant 4

HCID 962WaterHCID 1131751H-Benzotriazol-1-ol--ammonia (1/1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27588331,4-Benzodioxane-6-carboxylic Acid

Product 1

HCID 6592792,3-Dihydro-1,4-benzodioxine-6-carboxamideYield 31.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (3.54 g) in DMF (80 mL) were added HOBt-NH3 (4.48 g) and EDCI HCl (5.65 g) at room temperature. The reaction mixture was stirred at room temperature for 3 days, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was washed with hexane to give the title compound (1.10 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated aqueous sodium hydrogen carbonate solution and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. washthe residue was washed with hexane

Sources & evidence

ORD record
ord-0ed17a1e2b934c36a80c54d13e19d1c8
Source dataset
uspto-grants-2015_10
Patent number
US09150591B2

Reaction notes

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