Benzoin acetate → Oxazole, 2-methyl-4,5-diphenyl-

HRID 2271231Notes

Reaction equation

HRID 2271231 reaction equation
[C:1]([O:4][CH:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=O)[CH3:2].[NH2:20]C(N)=S>CN(C)C=O>[CH3:2][C:1]1[O:4][C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:20]=1

Participants

4

Reactant 2

HCID 95416Benzoin acetateHCID 2723790Thiourea

Product 1

HCID 139703Oxazole, 2-methyl-4,5-diphenyl-

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

0.2 g of the above 2-oxo-1,2-diphenylethyl acetate is dissolved in 10 ml of dimethylformamide in a reactor. 0.12 g of thiourea (2 eq.) is subsequently added and the reaction mixture is left to react at reflux (160° C.) for 10 hours. The reaction mixture is extracted using dichloromethane and then washed with water 3 times. The organic phase is recovered after separating by settling, dried over sodium sulphate, filtered and then concentrated to dryness under vacuum. The oil obtained is subsequently purified on a column of silica gel (elutent: dichloromethane).

Workup

  1. waitthe reaction mixture is left
  2. customto react
  3. extractionThe reaction mixture is extracted
  4. washwashed with water 3 times
  5. customThe organic phase is recovered
  6. customafter separating
  7. dry with materialdried over sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated to dryness under vacuum
  10. customThe oil obtained
  11. customis subsequently purified on a column of silica gel (elutent: dichloromethane)

Sources & evidence

ORD record
ord-8a7688708a3646f9a5e5e5cbf2e407d1
Source dataset
uspto-grants-2001_12
Patent number
US06333414B1

Reaction notes

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