Thionyl Chloride → HCID 20313050, compound

HRID 1659155Notes

Reaction equation

HRID 1659155 reaction equation
C([NH:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([OH:11])=O)=[C:7]([O:15][CH3:16])[CH:6]=1)(=O)C.S(Cl)(Cl)=O.[NH2:21][CH:22]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]1>>[NH2:4][C:5]1[C:13]([Cl:14])=[CH:12][C:8]([C:9]([NH:21][CH:22]2[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23]2)=[O:11])=[C:7]([O:15][CH3:16])[CH:6]=1

Participants

4

Reactant 3

HCID 24386Thionyl ChlorideHCID 109884964-Acetamido-5-chloro-2-methoxybenzoic acidHCID 189403961-Methylpyrrolidin-3-amine

Product 1

HCID 20313050HCID 20313050, compound

Procedure

A suspension of 5.3 g. (0.022 mole) of 4-acetamido-5-chloro-2-methoxybenzoic acid in 30 ml. of thionyl chloride was refluxed for two hours and then concentrated. To the concentrate was added 100 ml. of chloroform and the solution was again concentrated. The residue was again dissolved in chloroform and added at a rapid drop to a chloroform solution containing 2.4 g. (0.024 mole) of 3-amino-1-methylpyrrolidine. The solution was stirred for one hour and concentrated. The residue was dissolved in 100 ml. of 4N hydrochloric acid and the solution was refluxed for 10 minutes, cooled in an ice bath and basified with sodium hydroxide. The mixture was extracted with chloroform and the extract dried and concentrated. The crystalline residue was recrystallized from isopropyl ether-isopropyl alcohol followed by another recrystallization from ethyl acetate. The yield of product was 1.4 g. (22 %); m.p. 185°-187°C.

Workup

  1. additionA suspension of 5.3 g
  2. concentrationconcentrated
  3. additionTo the concentrate was added 100 ml
  4. concentrationof chloroform and the solution was again concentrated
  5. dissolutionThe residue was again dissolved in chloroform
  6. additionadded at a rapid drop to a chloroform solution
  7. additioncontaining 2.4 g
  8. concentrationconcentrated
  9. dissolutionThe residue was dissolved in 100 ml
  10. temperatureof 4N hydrochloric acid and the solution was refluxed for 10 minutes
  11. temperaturecooled in an ice bath
  12. extractionThe mixture was extracted with chloroform
  13. customthe extract dried
  14. concentrationconcentrated
  15. customThe crystalline residue was recrystallized from isopropyl ether-isopropyl alcohol
  16. customfollowed by another recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-9d914134bfef47d195d1d3568d20100b
Source dataset
uspto-grants-1976_06
Patent number
US03966957

Reaction notes

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