Dimethylformamide → HCID 13290064, compound

HRID 371000Notes

Reaction equation

HRID 371000 reaction equation
[Cl:1][C:2]1[C:3]([OH:14])=[CH:4][C:5]2[C:9]([CH3:10])=[C:8]([CH3:11])[S:7][C:6]=2[C:12]=1[Cl:13].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[CH2:20]([O:19][C:17](=[O:18])[CH2:16][O:14][C:3]1[C:2]([Cl:1])=[C:12]([Cl:13])[C:6]2[S:7][C:8]([CH3:11])=[C:9]([CH3:10])[C:5]=2[CH:4]=1)[CH3:21]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290063HCID 13290063, compound

Product 1

HCID 13290064HCID 13290064, compoundYield 85.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

To a mixture of 22.4 g of 6,7-dichloro-5-hydroxy-2,3-dimethylbenzo[b]thiophene is added a mixture of 18.23 g of ethyl bromoacetate in 100 ml of 2-butanone, followed by 15 g of potassium carbonate and 7.5 ml of sieve-dried dimethylformamide. The reaction mixture is stirred at 95°-100° for 21/2 hrs, allowed to cool and filtered. To the filtrate is added 100 ml of water and the mixture is extracted with ethyl ether. The organic layers are separated, washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give a solid. The solid is recrystallized from acetone-hexane to give 25.8 g of ethyl[(6,7-dichloro-2,3-dimethylbenzo[b]thien-5-yl)oxy]acetate, mp 102°-104°.

Workup

  1. additionis added
  2. temperatureto cool
  3. filtrationfiltered
  4. additionTo the filtrate is added 100 ml of water
  5. extractionthe mixture is extracted with ethyl ether
  6. customThe organic layers are separated
  7. washwashed
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. customthe solvent is removed
  11. customto give a solid
  12. customThe solid is recrystallized from acetone-hexane

Sources & evidence

ORD record
ord-3d1e5227b9ea49c4b07860d7ec3095b2
Source dataset
uspto-grants-1985_07
Patent number
US04528399

Reaction notes

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