Hydrochloric Acid → HCID 14391420, compound

HRID 1638239Notes

Reaction equation

HRID 1638239 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[C:10]=2[Cl:16])=[O:7])=[CH:4][CH:3]=1.Br[CH2:20][C:21]([OH:23])=[O:22].[OH-].[Na+].Cl>O1CCOCC1.O>[Cl:16][C:10]1[C:11]([Cl:15])=[CH:12][CH:13]=[CH:14][C:9]=1[NH:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:20][C:21]([OH:23])=[O:22])=[CH:18][CH:17]=1)=[O:7]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6227Bromoacetic AcidHCID 14798Sodium HydroxideHCID 12770927HCID 12770927, compound

Product 1

HCID 14391420HCID 14391420, compoundYield 73.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

2.82 g of 4-hydroxy-N-(2,3-dichlorophenyl)-benzamide and 1.67 g of bromoacetic acid were dissolved in 10 ml of dioxane. To this solution, a mixture of 0.97 g of sodium hydroxide and 2 ml of water was dropwise added over a period of 10 minutes at a temperature of 20° C. under stirring. After the dropwise addition, the reaction solution was stirred at a temperature of 80° C. for 2 hours. After completion of the reaction, the reaction solution was poured into 50 ml of water, and acidified with hydrochloric acid. Then, the crude product obtained by collecting precipitates by filtration, was recrystallized from toluene/methanol to obtain 2.5 g of desired 4-(2,3-dichlorophenyl-carbamoyl)-phenoxyacetic acid. Yield: 70.6% Melting point: 198°-199.5° C.

Workup

  1. additionwas dropwise added over a period of 10 minutes at a temperature of 20° C.
  2. additionAfter the dropwise addition
  3. stirringthe reaction solution was stirred at a temperature of 80° C. for 2 hours
  4. customAfter completion of the reaction
  5. customThen, the crude product obtained
  6. customby collecting
  7. customprecipitates by filtration
  8. customwas recrystallized from toluene/methanol

Sources & evidence

ORD record
ord-f6d14a15e87f43c2a26db376637be607
Source dataset
uspto-grants-1989_11
Patent number
US04878942

Reaction notes

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