Dimethylformamide → HCID 19744462, compound

HRID 2254419Notes

Reaction equation

HRID 2254419 reaction equation
O[CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:7]=1.CN(C)C=O.S(Cl)([Cl:20])=O.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl>[Cl:20][CH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8]2[CH:12]=[CH:11][S:10][CH:9]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 19744528HCID 19744528, compound

Product 1

HCID 19744462HCID 19744462, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

100 mg of 2-hydroxymethyl-4-(3-thienyl)thiophene was suspended in 5 ml of chloroform, and with stirring under ice cooling, 2 microliters of dimethylformamide and 80 microliters of thionyl chloride were added. The mixture was stirred for 30 minutes, and neutralized with a saturated aqueous solution of sodium hydrogen carbonate under ice cooling. The organic layer was separated, washed with a saturated aqueous solution of sodium chloride, and dried over anhydrous magnesium sulfate. The desiccant was separated by filtration, and the chloroform was evaporated to give 2-chloromethyl-4-(3-thienyl)thiophene as a yellow powder.

Workup

  1. stirringThe mixture was stirred for 30 minutes
  2. customThe organic layer was separated
  3. washwashed with a saturated aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe desiccant was separated by filtration
  6. customthe chloroform was evaporated

Sources & evidence

ORD record
ord-4297d911f9e64a3ca9f76c1e80ebc95f
Source dataset
uspto-grants-1993_08
Patent number
US05234946

Reaction notes

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