Dimethylformamide → HCID 13290078, compound

HRID 485924Notes

Reaction equation

HRID 485924 reaction equation
[Cl:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15].Br[CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[Cl:1][C:2]1[C:3]([O:16][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:4][C:5]2[CH:9]=[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])[S:7][C:6]=2[C:14]=1[Cl:15]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290077HCID 13290077, compound

Product 1

HCID 13290078HCID 13290078, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent2×

Procedure

To a mixture of 10 g of 6,7-dichloro-5-hydroxy-2-isobutylbenzo[b]thiophene and 200 ml 2-butanone is added a mixture of 6.9 g of ethyl bromoacetate in 50 ml of 2-butanone and by 6.6 g of potassium carbonate and 3.4 ml sieve-dried dimethylformamide. The reaction mixture is stirred at 95°-100° for 2 hrs, allowed to cool and filtered. To the filtrate is added 100 ml of water and 100 ml of ether. The organic layers are combined, washed, dried over anhydrous magnesium sulfate, filtered and the solvent is removed to give a solid. Recrystallization from ethyl ether and hexane gives 12 g of ethyl [(6,7-dichloro-2-isobutylbenzo[b]-thiene-5-yl)oxy]acetate, mp 75°-76°.

Workup

  1. additionis added
  2. temperatureto cool
  3. filtrationfiltered
  4. additionTo the filtrate is added 100 ml of water and 100 ml of ether
  5. washwashed
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. customthe solvent is removed
  9. customto give a solid
  10. customRecrystallization from ethyl ether and hexane

Sources & evidence

ORD record
ord-72db800366df485997fb65c781c41117
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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