Water → HCID 3757205, compound

HRID 1293112Notes

Reaction equation

HRID 1293112 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[NH:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[N:7]1.[OH-].[K+].O>CN(C)C=O.C(OCC)(=O)C>[Br:1][CH2:2][CH2:3][CH2:4][N:7]1[N:8]=[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[N:6]1

Participants

7

Reactant 4

HCID 962WaterHCID 80011,3-DibromopropaneHCID 14797Potassium HydroxideHCID 178418385HCID 178418385, compound

Product 1

HCID 3757205HCID 3757205, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 1,3-dibromopropane (510 μl, 5.0 mmol) in dimethylformamide (10 ml) was added benzotriazole (600 mg, 5.0 mmol) and KOH (430 mg, 7.7 mmol). After stirring for 20 h at room temp, water (10 ml) and ethyl acetate (10 ml) were added. The phases were separated and the aqueous phase was re-extracted with ethyl acetate (3×15 ml). The combined organic phases were dried over MgSO4 and concentrated in vacuo, giving 1.44 g of the crude material. The crude product was purified by flash chromatography (0–10% methanol in DCM), yielding 274 mg (23%) of the title compound 62. TLC (5% methanol in DCM): Rf=0.7. 1H-NMR (400 MHz, CDCl3): δ=7.88–7.83 (2H, m); 7.41–7.36 (2H, m); 4.91 (2H, t); 3.44 (2H, t); 2.66 (2H, m).

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was re-extracted with ethyl acetate (3×15 ml)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customgiving 1.44 g of the crude material
  6. customThe crude product was purified by flash chromatography (0–10% methanol in DCM)

Sources & evidence

ORD record
ord-5d5f641f8c724cb1a24c835b6dac6a81
Source dataset
uspto-grants-2007_07
Patent number
US07238713B2

Reaction notes

Loading…