Tetrahydrofuran → HCID 19766029, compound

HRID 1591038Notes

Reaction equation

HRID 1591038 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5](Cl)=[O:6].Cl.[NH2:12][C:13]1[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][C:14]=1O.[OH-].[Na+].C1COCC1>C(O)C.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:6][C:14]3[CH:15]=[C:16]([OH:17])[CH:18]=[CH:19][C:13]=3[N:12]=2)[CH:8]=[CH:9][CH:10]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69252Benzoyl chloride, 3-chloro-HCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 19766029HCID 19766029, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

4.5 ml (35.2 mmol) of 3-chlorobenzoyl chloride and 1.0 g (6.19 mmol) of 4-aminoresorcinol hydrochloride were introduced into a three-necked flask provided with a thermometer and a cooling condenser, and the mixture was heated at 170° to 235° C. for 1 hour, then the excessive acid chloride was removed by distillation. To the residue, 1.5 g (38.5 mmol) of NaOH, 20 ml of THF, 20 ml of water and 10 ml of ethanol were added, and the mixture was stirred at room temperature for about 2 hours. The reaction solution was extracted with ethyl acetate, the extract was washed with saturated sodium chloride water solution, and ethyl acetate was distilled off. Recrystallizing the residue with water/methanol/THF and drying the crystal, there was obtained 250 mg (1.02 mmol) of 2-(3-chlorophenyl)-6-hydroxybenzoxazole. The yield was 16.5%.

Workup

  1. customprovided with a thermometer and a cooling condenser
  2. temperaturethe mixture was heated at 170° to 235° C. for 1 hour
  3. customthe excessive acid chloride was removed by distillation
  4. extractionThe reaction solution was extracted with ethyl acetate
  5. washthe extract was washed with saturated sodium chloride water solution, and ethyl acetate
  6. distillationwas distilled off
  7. customRecrystallizing the residue with water/methanol/THF
  8. customdrying the crystal

Sources & evidence

ORD record
ord-318435ecc07d4049a9ea57f7ba3f80e4
Source dataset
uspto-grants-1993_04
Patent number
US05206149

Reaction notes

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