Hydrochloric Acid → HCID 12423621, compound

HRID 1447697Notes

Reaction equation

HRID 1447697 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]1[CH2:14][C:13]2[C:8](=[C:9]([Cl:17])[C:10]([Cl:16])=[C:11]([OH:15])[CH:12]=2)[C:7]1=[O:18].[C:19](=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29]CC)=[O:28].[OH-].[Na+].Cl>CN(C)C=O.O>[O:18]=[C:7]1[C:8]2[C:13](=[CH:12][C:11]([O:15][CH2:26][C:27]([OH:29])=[O:28])=[C:10]([Cl:16])[C:9]=2[Cl:17])[CH2:14][C:6]1([CH3:19])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 56617763HCID 56617763, compound

Product 1

HCID 12423621HCID 12423621, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-methyl-2-(2-thienyl-5-hydroxy-6,7-dichloro-1-indanone (3.13 g., 0.01 g., 0.01 mole), potassium carbonate (2.77 g., 0.02 mole) and ethyl bromoacetate (3.34 g., 0.02 mole) in dimethylformamide (40 ml.) is warmed at 55°-60° C. for 2 hours, then treated with water (40 ml.)-10 N sodium hydroxide solution (4 ml., 0.04 mole) and heated at 100° C. for one hour. The reaction mixture is added slowly to crushed ice-water (700 ml.)-12 N hydrochloric acid (10 ml.) to precipitate 1.78 g. of [1-oxo-2-methyl-2-(2-thienyl)-6,7-dichloro-5-indanyloxy]acetic acid which melts at 161°-162° C. after crystallization from nitromethane.

Workup

  1. temperatureis warmed at 55°-60° C. for 2 hours
  2. additionThe reaction mixture is added slowly
  3. customto precipitate 1.78 g
  4. customof [1-oxo-2-methyl-2-(2-thienyl)-6,7-dichloro-5-indanyloxy]acetic acid which melts at 161°-162° C. after crystallization from nitromethane

Sources & evidence

ORD record
ord-5e00ea7a36194920ad5fbbdbf6509931
Source dataset
uspto-grants-1979_12
Patent number
US04177285

Reaction notes

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