Diethyl Ether → N'-[(3-chlorobenzoyl)oxy]-2-hydroxypropanimidamide

HRID 732089Notes

Reaction equation

HRID 732089 reaction equation
[OH:1][N:2]=[C:3]([NH2:7])[CH:4]([OH:6])[CH3:5].[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12](Cl)=[O:13].CCOCC>C1COCC1>[Cl:8][C:9]1[CH:10]=[C:11]([CH:15]=[CH:16][CH:17]=1)[C:12]([O:1][N:2]=[C:3]([NH2:7])[CH:4]([OH:6])[CH3:5])=[O:13]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 69252Benzoyl chloride, 3-chloro-HCID 5063567N',2-dihydroxypropanimidamide

Product 1

HCID 76579670N'-[(3-chlorobenzoyl)oxy]-2-hydroxypropanimidamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

6.45 g crude N′,2-dihydroxypropanimidamide was cooled on an ice-bath with 23.5 mL DEA in THF (200 mL). To this slurry 21.94 g 3-chlorobenzoyl chloride was added. The mixture was warmed to r.t. and stirred for 2 h. Addition of Et2O (200 mL), washing with sat. aq. NH4Cl and re-extraction of the aq. layer gave after combining and concentration of the org. layers followed by drying in vacuo 27.24 g of crude title compound, which was used directly in the next step for 1-[5-(3-chlorophenyl)-[1,2,4]oxadiazol-3-yl]ethanol. LC-MS (M++1): 243

Workup

  1. washwashing with sat. aq. NH4Cl and re-extraction of the aq. layer
  2. customgave
  3. dry with materialby drying in vacuo 27.24 g of crude title compound, which

Sources & evidence

ORD record
ord-95b27508b95941378831e038a8b30121
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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