Tetrahydrofuran → HCID 19766035, compound

HRID 1591041Notes

Reaction equation

HRID 1591041 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.[NH2:13][C:14]1[CH:20]=[CH:19][C:17]([OH:18])=[CH:16][C:15]=1O.[OH-].[Na+].C1COCC1>CO.O>[Cl:1][C:2]1[CH:10]=[C:9]([Cl:11])[CH:8]=[CH:7][C:3]=1[C:4]1[O:5][C:15]2[CH:16]=[C:17]([OH:18])[CH:19]=[CH:20][C:14]=2[N:13]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 666452,4-Dichlorobenzoyl chlorideHCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 19766035HCID 19766035, compoundYield 26.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

9.9 ml (70.5 mmol) of 2,4-dichlorobenzoyl chloride and 2.0 g (12.4 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 172° to 247° C. for 1 hour, then excessive acid chloride was removed by distillation. To the residue, 6.47 g (161.8 mmol) of NaOH, 60 ml of THF, 60 μl 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 915 mg (3.27 mmol) of 2-(2,4-dichlorophenyl)-6-hydroxybenzoxazole. The yield was 26.3%.

Workup

  1. customprovided with a thermometer and a cooling condenser
  2. temperaturethe mixture was heated at 172° to 247° C. for 1 hour
  3. customexcessive 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-66c66956c2e1451bbf9a2dac97e52f4a
Source dataset
uspto-grants-1993_04
Patent number
US05206149

Reaction notes

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