Dimethylformamide → HCID 12083070, compound

HRID 1168850Notes

Reaction equation

HRID 1168850 reaction equation
Br[CH2:2][CH2:3][Cl:4].CN(C=O)C.[CH3:10][C:11]1[C:19]2[O:18][N:17]=[C:16]([OH:20])[C:15]=2[CH:14]=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>ClCCl.CO.O.C(OC(=O)C)C>[Cl:4][CH2:3][CH2:2][O:20][C:16]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([CH3:10])[C:19]=2[O:18][N:17]=1

Participants

9

Reactant 4

HCID 6228Dimethylformamide2×HCID 78491-Bromo-2-ChloroethaneHCID 11430Potassium CarbonateHCID 178423919HCID 178423919, compound

Product 1

HCID 12083070HCID 12083070, compoundYield 70%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Bromo-2-chloroethane (168 μl, 2.0 mmol) was added to 5 ml DMF in a 50 ml flask. 7-Methyl-benzo[d]isoxazol-3-ol (298 mg, 2.0 mmol), potassium carbonate (276 mg, 2.0 mmol) and additional DMF (5 ml) were added and the mixture was stirred for 12 h. Ethylacetate (50 ml) and H2O (50 ml) were added. The two phases were separated and the aqueous phase was extracted with ethylacetate. The combined organic phases were washed with brine, dried over MgSO4 and evaporated to dryness to give 420 mg of the crude product. The crude product was subjected to column chromatography (0-5% methanol in dichloromethane) to give the pure title compound 41 (290 mg, 70%). 1H NMR (CDCl3) 2.5 (s, 3H), 3.9 (t, 2H), 4.7 (t, 2H), 7.2 (t, 1H), 7.3 (d, 1H), 7.5 (d, 2H).

Workup

  1. customThe two phases were separated
  2. extractionthe aqueous phase was extracted with ethylacetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customto give 420 mg of the crude product

Sources & evidence

ORD record
ord-ad7f99385378447da58d0afe4f80a1c2
Source dataset
uspto-grants-2003_09
Patent number
US06627645B2

Reaction notes

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