HCID 136160556, compound → HCID 136160555, compound

HRID 1930182Notes

Reaction equation

HRID 1930182 reaction equation
O/[N:2]=[C:3](\[NH:13][C:14](=[O:22])[O:15]C1C=CC=CC=1)/[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([I:11])=[C:7]([CH3:12])[CH:6]=1>C1(C)C=CC=CC=1>[I:11][C:8]1[CH:9]=[CH:10][C:5]([CH2:4][C:3]2[NH:13][C:14](=[O:15])[O:22][N:2]=2)=[CH:6][C:7]=1[CH3:12]

Participants

3

Reactant 1

HCID 136160556HCID 136160556, compound2×

Product 1

HCID 136160555HCID 136160555, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(Z)-Phenyl 1-(hydroxyimino)-2-(4-iodo-3-methylphenyl)ethylcarbamate (Intermediate 29-2; 1.67 g, 4.07 mmol) was dissolved in anhydrous toluene (30 mL). The resulting solution was stirred at reflux for 16 hours. The cooled reaction mixture was evaporated to dryness and redissolved in DCM (50 mL) and extracted with saturated NaHCO3 (50 mL). The aqueous layer was acidified with 2M HCl and extracted with EtOAc (3×50 mL). The organic layers were combined and dried over MgSO4, filtered and evaporated to afford desired product. 3-(4-iodo-3-methylbenzyl)-1,2,4-oxadiazol-5(4H)-one (0.787 g, 61.2%) as a yellow solid.

Workup

  1. temperatureat reflux for 16 hours
  2. customThe cooled reaction mixture
  3. customwas evaporated to dryness
  4. dissolutionredissolved in DCM (50 mL)
  5. extractionextracted with saturated NaHCO3 (50 mL)
  6. extractionextracted with EtOAc (3×50 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-6f094819f495400a80994e8e616d4725
Source dataset
uspto-grants-2012_05
Patent number
US08188092B2

Reaction notes

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