Sodium Chloride → HCID 15547442, compound

HRID 324182Notes

Reaction equation

HRID 324182 reaction equation
C1N[C:4](=[O:5])NC1.[NH2:7][C:8]1[C:13]([OH:14])=[CH:12][C:11]([C:15]2[O:19][CH2:18][C:17]([CH3:21])([CH3:20])[C:16]=2[C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:10][C:9]=1[OH:26].[Cl-].[Na+]>>[C:22]([C:16]1[C:17]([CH3:20])([CH3:21])[CH2:18][O:19][C:15]=1[C:11]1[CH:10]=[C:9]([OH:26])[C:8]2[N:7]=[C:15]([C:11]3[CH:12]=[CH:13][C:8]([O:5][CH3:4])=[CH:9][CH:10]=3)[O:14][C:13]=2[CH:12]=1)([CH3:25])([CH3:24])[CH3:23]

Participants

4

Reactant 3

HCID 5234Sodium ChlorideHCID 84532-ImidazolidinoneHCID 15547431HCID 15547431, compound2×

Product 1

HCID 15547442HCID 15547442, compoundYield 81.9%

Conditions

Temperature
150 °C

Procedure

In nitrogen atmosphere at a room temperature, to 310 mg (1.46 mmol) of trimethyl 4-methoxy-1-orthobenzoate was added 1 ml of ethyleneurea dissolving 133 mg (0.48 mmol) of 5-(4-amino-3,5-dihydrophenyl)-4-t-butyl-3,3-dimethyl-2,3-dihydrofuran (Compound [8]), and the mixture was heated for 1.0 hours at 150° C. The resulting mixture was poured in saturated aqueous solution of sodium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, dried with magnesium sulfate anhydride, and concentrated. The residue was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane: ethyl acetate=3:1), and then followed by recrystallization from the mixture of methylene chloride and hexane to obtain 155 mg of 4-t-butyl-5-(4-hydroxy-2-(p-methoxyphenyl)benzo[d]-oxazol-6-yl)-3,3-dimethyl-2,3-dihydrofuran (Compound [67]) as a colorless granular micro-crystal. Yield 81.9%.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  3. dry with materialdried with magnesium sulfate anhydride
  4. concentrationconcentrated
  5. washthe elution
  6. additionwas carried out with the mixture of hexane and ethyl acetate (hexane: ethyl acetate=3:1)
  7. customfollowed by recrystallization from the mixture of methylene chloride and hexane

Sources & evidence

ORD record
ord-e6cf7c3ccdbe4797bc18814211033d30
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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