Hydrochloric Acid → HCID 178517504, compound

HRID 1880662Notes

Reaction equation

HRID 1880662 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]([NH2:10])=O)[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[C:15](N1C=CN=C1)(N1C=CN=C1)=[O:16].[N:27]12CCCN=C1CCCCC2.[ClH:38].[OH2:39]>O1CCCC1>[Cl:38][C:2]1[N:7]=[C:6]([C:8]2[NH:27][O:39][C:15](=[O:16])[N:10]=2)[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86647326HCID 86647326, compound

Product 1

HCID 178517504HCID 178517504, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1 ml of tetrahydrofuran were added 0.07 g of 6-chloro-4-trifluoromethylpyridine-2-carboxamide=oxime and 0.057 g of 1,1′-carbonyldiimidazole, and the mixture was stirred at room temperature for 3 hours. Thereafter, 0.053 g of 1,8-diazabicyclo[5,4,0]undec-7-ene was added, and the mixture was stirred for 6 hours. To the reaction solution were added water and 10% HCl, the resultant solution was extracted with ethyl acetate three times, and the organic layers were combined, dried with anhydrous magnesium sulfate, and concentrated. The residue was subjected to silica gel column chromatography to obtain 0.058 g of 3-(6-chloro-4-trifluoromethylpyridin-2-yl)-1,2,4-oxadiazol-5-one (present compound (1)).

Workup

  1. stirringthe mixture was stirred for 6 hours
  2. extractionthe resultant solution was extracted with ethyl acetate three times
  3. dry with materialdried with anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-a6a151c73bac47ffb94084bcb03b323f
Source dataset
uspto-grants-2012_11
Patent number
US08318776B2

Reaction notes

Loading…