Dimethylformamide → HCID 13290049, compound

HRID 485905Notes

Reaction equation

HRID 485905 reaction equation
[CH2:1]([C:5]1[S:9][C:8]2[C:10]([Cl:16])=[C:11]([Cl:15])[C:12]([OH:14])=[CH:13][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4].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.CCOCC.O>[CH2:1]([C:5]1[S:9][C:8]2[C:10]([Cl:16])=[C:11]([Cl:15])[C:12]([O:14][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:13][C:7]=2[CH:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 13290048HCID 13290048, compound

Product 1

HCID 13290049HCID 13290049, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture of 2-n-butyl-6,7-dichloro-5-hydroxybenzo[b]thiophene, 3.6 g of ethyl bromoacetate, 3.2 g of potassium carbonate and 4 ml dimethylformamide in 50 ml of 2-butanone is refluxed for 20 hrs. The cooled mixture is poured into 100 ml water and 100 ml ether. The layers are separated and the aqueous layer is extracted with two 100-ml portions of ether. The organic layers are combined, dried over anhydrous magnesium sulfate, filtered and the solvent is removed. Recrystallization from ether-hexane gives 4.1 g of ethyl [(2-n-butyl-6,7-dichlorobenzo[b]thien-5-yl)oxy]acetate, mp 72°-73°.

Workup

  1. temperatureis refluxed for 20 hrs
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with two 100-ml portions of ether
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent is removed
  7. customRecrystallization from ether-hexane

Sources & evidence

ORD record
ord-aed558cf1b9e476eb009fefca8138e13
Source dataset
uspto-grants-1985_08
Patent number
US04537976

Reaction notes

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