1,2-Dichloroethane → HCID 19002342, compound

HRID 2260019Notes

Reaction equation

HRID 2260019 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2(C(O)=O)[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[S:13][CH2:12]2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].ClC[CH2:25][Cl:26].S(Cl)(Cl)=[O:28]>CN(C=O)C>[Cl:26][C:25]([C:12]1[S:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:11]=1[C:5]1[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=1)=[O:28]

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 24386Thionyl ChlorideHCID 19002365HCID 19002365, compound

Product 1

HCID 19002342HCID 19002342, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(3,4-Dimethoxyphenyl)benzothiophene-3-carboxylic acid (25 g; 0.08 mole) prepared according to process D, 1,2-dichloroethane (300 ml ), thionyl chloride (12 ml, 0.16 mole) and DMF (1 ml) are introduced into a flask. The mixture is progressively heated to reflux temperature; the solid dissolves little by little to provide a clear yellow solution. After four hours, the solvents are evaporated to provide 2-(chlorocarbonyl)-3-(3,4-dimethoxyphenyl)benzothiophene (24.7 g; yield=96%).

Workup

  1. additionare introduced into a flask
  2. temperatureThe mixture is progressively heated
  3. temperatureto reflux temperature
  4. dissolutionthe solid dissolves little by little
  5. customto provide a clear yellow solution
  6. customthe solvents are evaporated

Sources & evidence

ORD record
ord-238509cc6f624914a410c74507912046
Source dataset
uspto-grants-1995_12
Patent number
US05475132

Reaction notes

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