Hydrochloric Acid → HCID 21527348, compound

HRID 1659186Notes

Reaction equation

HRID 1659186 reaction equation
[CH3:1][C:2]1([C:16]2[S:17][CH:18]=[CH:19][CH:20]=2)[C:10](=[O:11])[C:9]2[C:4](=[CH:5][C:6]([OH:14])=[C:7]([Cl:13])[C:8]=2[Cl:12])[C:3]1=[O:15].C(=O)([O-])[O-].[K+].[K+].Br[CH2:28][C:29]([O:31]CC)=[O:30].[OH-].[Na+].Cl>CN(C)C=O.O>[O:15]=[C:3]1[C:4]2[C:9](=[C:8]([Cl:12])[C:7]([Cl:13])=[C:6]([O:14][CH2:28][C:29]([OH:31])=[O:30])[CH:5]=2)[C:10](=[O:11])[C:2]1([CH3:1])[C:16]1[S:17][CH:18]=[CH:19][CH:20]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 21481326HCID 21481326, compound

Product 1

HCID 21527348HCID 21527348, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A stirred mixture of 2-methyl-2-(2-thienyl)-4,5-dichloro-6-hydroxyindan-1,3-dione (3.26 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 hrs., then treated with water (40 ml.) and 10N sodium hydroxide solution (4 ml., 0.04 mole) and heated at 100°C. for 1 hr. The reaction mixture is added slowly to crushed ice-water (700 ml.)-12N hydrochloric acid (10 ml.) to precipitate [1,3-dioxo-2-methyl-2-(2-thienyl)-4,5-dichloro-6-indanyloxy]acetic acid.

Workup

  1. temperatureis warmed at 55°-60°C. for 2 hrs
  2. additionThe reaction mixture is added slowly
  3. customto precipitate [1,3-dioxo-2-methyl-2-(2-thienyl)-4,5-dichloro-6-indanyloxy]acetic acid

Sources & evidence

ORD record
ord-911ea1305634436cad341869677d2a70
Source dataset
uspto-grants-1976_06
Patent number
US03966966

Reaction notes

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