Water → HCID 66812218, compound

HRID 1099568Notes

Reaction equation

HRID 1099568 reaction equation
[CH2:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16](=[O:19])[CH2:17][N:18]=3)=[CH:10][CH:9]=2)=[CH:5][CH:4]=1)[CH3:2].[CH:22]([O:25][C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)([CH3:24])[CH3:23].C(N(CC)CC)C.O>C1C=CC=CC=1>[CH2:1]([C:3]1[CH:21]=[CH:20][C:6]([O:7][C:8]2[CH:9]=[CH:10][C:11]([C:14]3[O:15][C:16](=[O:19])/[C:17](=[CH:30]/[C:29]4[CH:32]=[CH:33][C:26]([O:25][CH:22]([CH3:24])[CH3:23])=[CH:27][CH:28]=4)/[N:18]=3)=[CH:12][CH:13]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 2500774-IsopropoxybenzaldehydeHCID 66812510HCID 66812510, compound

Product 1

HCID 66812218HCID 66812218, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of N-[4-(4-ethylphenoxy)benzoyl]glycine (200 mg, 0.668 mmol) prepared in Example 89 (89a) and acetic anhydride (0.38 mL, 4.03 mmol) was stirred at 80° C. for 20 minutes. Ethyl acetate was added to the reaction mixture, and then the mixture was cooled to room temperature. The solvent was evaporated, and then the residue was purified by silica gel column chromatography (hexane:ethyl acetate, 3:1, v/v) to give 2-[4-(4-ethylphenoxy)phenyl]-1,3-oxazol-5(4H)-one (120 mg, 0.427 mmol). All of this 2-[4-(4-ethylphenoxy)phenyl]-1,3-oxazol-5(4H)-one was dissolved in benzene (0.9 mL), and then 4-isopropoxybenzaldehyde (71 mg, 0.432 mmol) and triethylamine (24 μL, 0.172 nmol) were added thereto. The mixture was stirred at 90° C. for 2 hours. After the addition of water to the reaction solution, the mixture was extracted with a solvent mixture of hexane and ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, and then concentrated to give 181 mg of the title compound (brown oil, yield: 99%).

Workup

  1. extractionthe mixture was extracted with a solvent mixture of hexane and ethyl acetate
  2. washwashed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ca706f34f35a46a993c58bfcd9e6a568
Source dataset
uspto-grants-2012_03
Patent number
US08143446B2

Reaction notes

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