Dimethylformamide → HCID 13290027, compound

HRID 652638Notes

Reaction equation

HRID 652638 reaction equation
[Cl:1][C:2]1[C:3]([OH:18])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[S:7][C:6]=2[C:16]=1[Cl:17].Br[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].C(=O)(O)[O-].[Na+].CN(C)C=O>CC(=O)CC>[CH2:24]([O:23][C:21](=[O:22])[CH2:20][O:18][C:3]1[C:2]([Cl:1])=[C:16]([Cl:17])[C:6]2[S:7][C:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:9][C:5]=2[CH:4]=1)[CH3:25]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 516892Sodium BicarbonateHCID 13290026HCID 13290026, compound

Product 1

HCID 13290027HCID 13290027, compoundYield 71.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 5.1 g of 6,7-dichloro-5-hydroxy-2-phenylbenzo[b]thiophene. 3.5 g of ethyl bromoacetate and 5 g of sodium bicarbonate in 100 ml of 2-butanone containing 10 ml of dimethylformamide is stirred at 85°-90° for 16 hours. The mixture is concentrated at reduced pressure to remove the sovents and the residue is triturated with 50 g of ice-water. After 30 minutes the solid is filtered and air dried. Recrystallization from ether-hexane gives 4.7 g of ethyl[(6,7-dichloro-2-phenylbenzo[b]thien-5-yl)oxy]acetate as fine needles, mp 116.5°-117°.

Workup

  1. concentrationThe mixture is concentrated at reduced pressure
  2. customto remove the sovents
  3. customthe residue is triturated with 50 g of ice-water
  4. filtrationAfter 30 minutes the solid is filtered
  5. customair dried
  6. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-39cf447702a642968ceee7a9fe8c059e
Source dataset
uspto-grants-1987_06
Patent number
US04672138

Reaction notes

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