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 1798304노트

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HRID 1798304 반응식
[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

참가 물질

5

반응물 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

생성물 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)acetate수율 82.7%

시약·촉매·용매 3

HCID 313Hydrochloric Acid촉매HCID 702Ethanol용매HCID 962Water용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-3b41c1d75ef24e2eab5bec8274e55353
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08343944B2

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