Potassium Carbonate → HCID 53906177, compound

HRID 1416314Notes

Reaction equation

HRID 1416314 reaction equation
Cl[C:2]1[O:3][C:4]([C:8]([O:10][CH3:11])=[O:9])=[C:5](C)[N:6]=1.N[C:13](N)=[S:14].Br[CH2:17][CH2:18][CH:19]=[C:20]([F:22])[F:21].C(=O)([O-])[O-].[K+].[K+]>C(O)C.CC(C)=O>[F:21][C:20]([F:22])=[CH:19][CH2:18][CH2:17][S:14][CH2:13][C:2]1[O:3][C:4]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][N:6]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2723790ThioureaHCID 27822404-Bromo-1,1-difluorobut-1-eneHCID 12993967Methyl 2-chloro-4-methyl-1,3-oxazole-5-carboxylate

Product 1

HCID 53906177HCID 53906177, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

The product from Step 2 (0.176 g) and thiourea (0.084 g) were stirred in ethanol (5 cm3) and heated to reflux under an atmosphere of nitrogen for 5 hours. The reaction was cooled and solvent removed by evaporation under reduced pressure to give a yellow gum which was dissolved in acetone containing 4-bromo-1,1-difluorobut-1-ene (0.17 g) and potassium carbonate (0.2 g). This mixture was stirred for 1 hour under an atmosphere of nitrogen at ambient temperature and stored for 18 hours. The solvent was evaporated under reduced pressure and the residue treated with water and diethyl ether. The organic phase was separated, dried (MgSO4) and evaporated to give Compound VI.32 (0.095 g); M+ =175. 1H NMR: δ 2.45(5H,m); 3.22 (2H,t); 3.90(3H,s); 4.25(1H,m); (oil).

Workup

  1. temperatureheated
  2. temperatureto reflux under an atmosphere of nitrogen for 5 hours
  3. temperatureThe reaction was cooled
  4. customsolvent removed by evaporation under reduced pressure
  5. customto give a yellow gum which
  6. waitstored for 18 hours
  7. customThe solvent was evaporated under reduced pressure
  8. additionthe residue treated with water and diethyl ether
  9. customThe organic phase was separated
  10. dry with materialdried (MgSO4)
  11. customevaporated
  12. customto give Compound VI.32 (0.095 g)

Sources & evidence

ORD record
ord-6d1a2e815edb4bd78eb6c4d16783f99d
Source dataset
uspto-grants-1999_06
Patent number
US05912243

Reaction notes

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