Dimethylformamide → HCID 20185586, compound

HRID 2309573Notes

Reaction equation

HRID 2309573 reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].S(Cl)(Cl)=O.CN(C)[CH:18]=[O:19].[CH2:21]([Cl:23])Cl>C(O)(=O)C.C(O)C.O>[Cl:23][C:21]1([CH2:8][C:9]([C:5]2[CH:6]=[CH:7][C:2]([O:19][CH3:18])=[C:3]([CH2:8][C:9]([OH:11])=[O:10])[CH:4]=2)=[O:10])[CH:4]=[CH:3][CH:2]=[CH:7][CH2:6]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6344DichloromethaneHCID 17124o-Chlorophenylacetic acidHCID 24386Thionyl Chloride

Product 1

HCID 20185586HCID 20185586, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

17 g of 2-chloro-benzeneacetic acid, 10 ml of thionyl chloride, 0.5 ml of dimethyl formamide and 150 ml of methylene chloride are boiled for 6 hours. The solution is evaporated, and the residue is dissolved in 18 g of methyl 2-methoxy-benzeneacetate and 50 ml of methylene chloride. The resultant solution is added dropwise to a solution of 50 ml tin chloride in 250 ml methylene chloride. The solution is boiled for 24 hours, poured onto ice water, extracted with chloroform, dried and treated with active carbon. The chloroform solution is evaporated and the residue is recrystallized from ethanol. Hydrolysis of the crystals in 200 ml of 1M sodium hydroxide is followed by dilution with water and 50 ml ethanol to a volume of about 300 ml, whereupon the solution is acidified with acetic acid while boiling. It is then cooled, and the crystals are filtered off.

Workup

  1. customThe solution is evaporated
  2. dissolutionthe residue is dissolved in 18 g of methyl 2-methoxy-benzeneacetate
  3. additionThe resultant solution is added dropwise to a solution of 50 ml tin chloride in 250 ml methylene chloride
  4. additionpoured onto ice water
  5. extractionextracted with chloroform
  6. customdried
  7. additiontreated with active carbon
  8. customThe chloroform solution is evaporated
  9. customthe residue is recrystallized from ethanol
  10. customHydrolysis of the crystals in 200 ml of 1M sodium hydroxide
  11. temperatureIt is then cooled
  12. filtrationthe crystals are filtered off

Sources & evidence

ORD record
ord-456530a76d1b4d4ba0c2e737feb09c47
Source dataset
uspto-grants-1987_09
Patent number
US04695648

Reaction notes

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