Dimethylformamide → HCID 19347981, compound

HRID 1637189Notes

Reaction equation

HRID 1637189 reaction equation
[C:1]([O-:4])(=[O:3])[CH3:2].[Na+].Br[CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[C:15]([Cl:16])=[C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[S:13][C:12]=2[CH:22]=1.CN(C)C=O>O1CCCC1>[Cl:16][C:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][O:4][C:1]([CH3:2])=[O:3])=[CH:22][C:12]=2[S:13][C:14]=1[C:17]([O:19][CH2:20][CH3:21])=[O:18]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517045Sodium AcetateHCID 19347979HCID 19347979, compound

Product 1

HCID 19347981HCID 19347981, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

Sodium acetate (3.3 g, 40.5 mmol) was added to a stirred solution of ethyl 6-bromomethyl-3-chlorobenzo[b]thiophene-2-carboxylate (Preparation 10, 4.5 g, 13.5 mmol) in a mixture of anhydrous dimethylformamide (20 ml) and anhydrous tetrahydrofuran (10 ml), under a nitrogen atmosphere. The mixture was heated at 80° C. for 20 hours, then the mixture was partitioned between diethyl ether and water. The organic layer was separated and washed with more water, dried (magnesium sulfate), and evaporated under reduced pressure. The residue was flash chromatographed on silica gel using dichloromethane as eluant to give the title compound as a colourless gum (2.66 g).

Workup

  1. customthe mixture was partitioned between diethyl ether and water
  2. customThe organic layer was separated
  3. washwashed with more water
  4. dry with materialdried (magnesium sulfate)
  5. customevaporated under reduced pressure
  6. customchromatographed on silica gel

Sources & evidence

ORD record
ord-f9a63790c4f64f6a95d41b41bd6f9ee7
Source dataset
uspto-grants-2000_03
Patent number
US06040309

Reaction notes

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