Tetrahydrofuran → HCID 19766031, compound

HRID 1591039Notes

Reaction equation

HRID 1591039 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.Cl.[NH2:12][C:13]1[CH:19]=[CH:18][C:16]([OH:17])=[CH:15][C:14]=1O.[OH-].[Na+].C1COCC1>CO.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:7][C:14]3[CH:15]=[C:16]([OH:17])[CH:18]=[CH:19][C:13]=3[N:12]=2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 85014-Chlorobenzoyl chlorideHCID 14798Sodium HydroxideHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 19766031HCID 19766031, compoundYield 27.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

25 g (142.8 mmol) of 4-chlorobenzoyl chloride and 3.0 g (18.6 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 200° C. for 1 hour, then the excessive acid chloride was removed by distillation. To the residue, 8.4 g (210 mmol) of NaOH, 60 ml of THF, 60 ml of water and 30 ml of methanol 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 1.24 g (5.05 mmol) of 2-(4-chlorophenyl)-6-hydroxybenzoxazole. The yield was 27.2%.

Workup

  1. customprovided with a thermometer and a cooling condenser
  2. temperaturethe mixture was heated at 170° to 200° 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-84d0e2a7cc26477a95aa49f044373af8
Source dataset
uspto-grants-1993_04
Patent number
US05206149

Reaction notes

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