Sodium Hydroxide → HCID 19766033, compound

HRID 1591037Notes

Reaction equation

HRID 1591037 reaction equation
[Br: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+]>CO>[Br: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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 74377Benzoyl chloride, 3-bromo-HCID 134088224-Aminobenzene-1,3-diol hydrochloride

Product 1

HCID 19766033HCID 19766033, compoundYield 22.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

14.1 ml (107 mmol) of 3-bromobenzoic chloride and 1.7 g (10.5 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 90° to 145° C. for 30 minutes. To the residue, an aqueous solution of sodium hydroxide and methanol were added into a homogeneous solution which was then stirred at room temperature for 2 hours. The reaction solution was extracted twice with ethyl acetate and washed with 1N hydrochloric acid then with a saturated sodium chloride solution. Distilling off the excessive ethyl acetate, the obtained precipitate was recrystallized with THF/water. There was obtained 0.68 g (2.35 mmol) of 2-(3-bromophenyl)-6-hydroxybenzoxazole, and the yield was 16.6%.

Workup

  1. customprovided with a thermometer and a cooling condenser
  2. temperaturethe mixture was heated at 90° to 145° C. for 30 minutes
  3. extractionThe reaction solution was extracted twice with ethyl acetate
  4. washwashed with 1N hydrochloric acid
  5. distillationDistilling off the excessive ethyl acetate
  6. customthe obtained precipitate was recrystallized with THF/water

Sources & evidence

ORD record
ord-8811506cc97249fea4db51a031dced93
Source dataset
uspto-grants-1993_04
Patent number
US05206149

Reaction notes

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