Potassium Carbonate → 3-Benzo[1,3]dioxol-5-yl-5-bromomethyl-[1,2,4]oxadiazole

HRID 415682Notes

Reaction equation

HRID 415682 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].O[NH:7][C:8]([C:10]1[CH:18]=[CH:17][C:13]2[O:14][CH2:15][O:16][C:12]=2[CH:11]=1)=[NH:9].C([O-])([O-])=O.[K+].[K+]>O>[O:14]1[C:13]2[CH:17]=[CH:18][C:10]([C:8]3[N:7]=[C:3]([CH2:2][Br:1])[O:4][N:9]=3)=[CH:11][C:12]=2[O:16][CH2:15]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 178513224N-Hydroxybenzo[d][1,3]dioxole-5-carboximidamide

Product 1

HCID 594029623-Benzo[1,3]dioxol-5-yl-5-bromomethyl-[1,2,4]oxadiazoleYield 32.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

Bromoacetyl bromide (0.22 g, 1.10 mmol) was added to N-Hydroxy-benzo[1,3]dioxole-5-carboxamidine (0.40 g, 0.55 mmol) and K2CO3 (0.38 g, 0.78 mmol). The reaction mixture was heated at 100° C. for 15 min. After the completion of the reaction mixture (TLC monitoring), water (25 mL) was added and extracted with ethyl acetate (3×50 mL). The combined organics was washed with water, brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (60-120 M, 5% EtOAc-Hexane) to get the desired product (0.05 g, 31%).

Workup

  1. extractionextracted with ethyl acetate (3×50 mL)
  2. washThe combined organics was washed with water, brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified over silica gel (60-120 M, 5% EtOAc-Hexane)

Sources & evidence

ORD record
ord-7dd4de23f2834ae594942ccaaf975e82
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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