Potassium Hydroxide → HCID 67500957, compound

HRID 1919318Notes

Reaction equation

HRID 1919318 reaction equation
[OH-].[K+].[F:3][C:4]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[CH:6][CH:5]=1.[CH2:12]([N:14]([CH2:20][CH3:21])[C:15](=[O:19])[CH2:16][N+:17]#[C-:18])[CH3:13]>CO>[CH2:12]([N:14]([CH2:20][CH3:21])[C:15]([C@H:16]1[C@H:8]([C:7]2[CH:10]=[CH:11][C:4]([F:3])=[CH:5][CH:6]=2)[O:9][CH:18]=[N:17]1)=[O:19])[CH3:13]

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 680234-FluorobenzaldehydeHCID 12179642HCID 12179642, compound

Product 1

HCID 67500957HCID 67500957, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of KOH (0.26 g, 3.92 mmol) in MeOH (36 mL) was added successively 4-fluorobenzaldehyde (0.443 g, 3.56 mmol) and N,N-diethyl-2-isocyanoacetamide (0.50 g, 3.57 mmol). The solution was stirred for 16 h (0° C. to RT) and then concentrated. The residue was partitioned between CH2Cl2 (20 mL) and brine (20 mL). The organic layer was separated and the desired product was extracted with CH2Cl2 (3×20 mL). The combined organic layers were washed with brine (30 mL), dried over MgSO4, filtered and evaporated. A pale crude yellow solid was obtained the (±)-trans-N,N-diethyl-5-(4-fluorophenyl)-4,5-dihydrooxazole-4-carboxamide, SLA 19142, as a brown oil (0.86 g, 91% yield).

Workup

  1. stirringThe solution was stirred for 16 h (0° C. to RT)
  2. concentrationconcentrated
  3. customThe residue was partitioned between CH2Cl2 (20 mL) and brine (20 mL)
  4. customThe organic layer was separated
  5. extractionthe desired product was extracted with CH2Cl2 (3×20 mL)
  6. washThe combined organic layers were washed with brine (30 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-35c0c468b3b7460087426975f0fd38f0
Source dataset
uspto-grants-2012_05
Patent number
US08168631B2

Reaction notes

Loading…