Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate → Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

HRID 1798304Notes

Reaction equation

HRID 1798304 reaction equation
[Cl:1][C:2]1[C:10]2[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=2[CH:5]=[C:4]([O:18][C:19]2[S:20][C:21]([N+:24]([O-])=O)=[N:22][N:23]=2)[CH:3]=1>CCO.O.Cl>[NH2:24][C:21]1[S:20][C:19]([O:18][C:4]2[CH:3]=[C:2]([Cl:1])[C:10]3[CH:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:8][B:7]([OH:17])[C:6]=3[CH:5]=2)=[N:23][N:22]=1

Participants

5

Reactant 1

HCID 58292595Ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate

Product 1

HCID 58292780Ethyl 2-(6-(5-amino-1,3,4-thiadiazol-2-yloxy)-4-chloro-1-hydroxy-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetateYield 82.7%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of ethyl 2-(4-chloro-1-hydroxy-6-(5-nitro-1,3,4-thiadiazol-2-yloxy)-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl)acetate (430 mg, 1.08 mmol) in EtOH (15 mL) and H2O (5 mL) was added 2 drops of conc. HCl and the mixture was heated to reflex for 2 h. Upon cooling, the reaction mixture was filtered and the EtOH was removed under the reduced pressure and the residue was extracted with EtOAc (3×10 ml). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo to give the crude product as a yellow oil (330 mg). MS (ESI) m/z=370 [M+H]+.

Workup

  1. temperaturethe mixture was heated
  2. temperatureUpon cooling
  3. filtrationthe reaction mixture was filtered
  4. customthe EtOH was removed under the reduced pressure
  5. extractionthe residue was extracted with EtOAc (3×10 ml)
  6. dry with materialThe combined organic layers were dried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3b41c1d75ef24e2eab5bec8274e55353
Source dataset
uspto-grants-2013_01
Patent number
US08343944B2

Reaction notes

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