Water → tert-Butyl [2-(5-oxo-4,5-dihydro[1,3,4]oxadiazol-2-yl)thiophen-3-yl]carbamate

HRID 460314Notes

Reaction equation

HRID 460314 reaction equation
[C:1](Cl)(Cl)=[O:2].[C:5]([O:9][C:10]([NH:12][C:13]1[CH:17]=[CH:16][S:15][C:14]=1[C:18]([NH:20][NH2:21])=[O:19])=[O:11])([CH3:8])([CH3:7])[CH3:6].O>C1COCC1>[O:2]=[C:1]1[O:19][C:18]([C:14]2[S:15][CH:16]=[CH:17][C:13]=2[NH:12][C:10](=[O:11])[O:9][C:5]([CH3:8])([CH3:6])[CH3:7])=[N:20][NH:21]1

Participants

5

Reactant 3

HCID 962WaterHCID 6371PhosgeneHCID 184459443-(tert-Butoxycarbonylamino)thiophene-2-carboxylic hydrazide

Product 1

HCID 86760474tert-Butyl [2-(5-oxo-4,5-dihydro[1,3,4]oxadiazol-2-yl)thiophen-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4 ml of a 20% toluenic phosgene solution are added dropwise to a solution of 240 mg of 3-(tert-butoxycarbonylamino)thiophene-2-carboxylic hydrazide in 5 ml of THF and the mixture is stirred at RT. After one hour, the mixture is admixed with 10 ml of water and, after brief digestion, extracted with ethyl acetate. After the ethyl acetate phase has been dried over sodium sulfate, the mixture is concentrated under reduced pressure and the remaining residue is used further without further purification.

Workup

  1. extractionafter brief digestion, extracted with ethyl acetate
  2. dry with materialAfter the ethyl acetate phase has been dried over sodium sulfate
  3. concentrationthe mixture is concentrated under reduced pressure
  4. customthe remaining residue is used further without further purification

Sources & evidence

ORD record
ord-37189ac45f724e52911353c37347c860
Source dataset
uspto-grants-2007_03
Patent number
US07196114B2

Reaction notes

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