Phosgene → HCID 23319714, compound

HRID 1981597Notes

Reaction equation

HRID 1981597 reaction equation
C(Cl)(Cl)=O.[Cl:5][C:6]([N:8]([CH2:16][CH2:17][C:18](Cl)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=1)=[O:7].[Cl-].[Al+3].[Cl-].[Cl-]>C(Cl)Cl>[Cl:5][C:6]([N:8]1[C:9]2[C:14](=[CH:13][CH:12]=[C:11]([Cl:15])[CH:10]=2)[C:18](=[O:19])[CH2:17][CH2:16]1)=[O:7]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 6451240Aluminum(III) ChlorideHCID 53984224HCID 53984224, compound

Product 1

HCID 23319714HCID 23319714, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In an apparatus idenntical to that used in Example 1, methylene chloride (25 cc) is introduced. A stream of phosgene is then passed through for 10 minutes at a temperature in the region of 20° C., in order to remove the water and ethanol present in the solvent used. The phosgene dissolved is removed by passing a stream of argon through the solution for 20 minutes at a temperature in the region of 40° C. N-Chloroformyl-3-(m-chloroanilino)propionic acid chloride (2 g; 7.13 mmol) is then added, while working under an atmosphere of argon at a temperature of 26° C. Anhydrous aluminum chloride (2.09 g) is then added in the course of 10 minutes, the temperature changing from 26° to 32° C. The reaction mixture then consists of a yellow liquid phase and a suspension. The mixture is left to react for 15 hours at a temperature in the region of 20° C., and the reaction mixture is then poured onto ice (25 g). The organic phase is separated by decantation. The aqueous phase is extracted with methylene chloride (4×25 cc). The combined organic extracts are washed with water (4×25 cc) and then dried over sodium sulphate. After filtration, the filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C. 1-Chloroformyl-7-chloro-1,2,3,4-tetrahydro-4-quinolinone (1.5 g), m.p. 150°-153° C., is thus obtained which, after recrystallisation in ethyl acetate, melts at 156° C.

Workup

  1. additionis introduced
  2. customis then passed through for 10 minutes at a temperature in the region of 20° C., in order
  3. customto remove the water and ethanol present in the solvent
  4. dissolutionThe phosgene dissolved
  5. customis removed
  6. customfor 20 minutes
  7. customin the region of 40° C
  8. customwhile working under an atmosphere of argon at a temperature of 26° C
  9. customchanging from 26° to 32° C
  10. waitThe mixture is left
  11. customto react for 15 hours at a temperature in the region of 20° C.
  12. additionthe reaction mixture is then poured onto ice (25 g)
  13. customThe organic phase is separated by decantation
  14. extractionThe aqueous phase is extracted with methylene chloride (4×25 cc)
  15. washThe combined organic extracts are washed with water (4×25 cc)
  16. dry with materialdried over sodium sulphate
  17. filtrationAfter filtration
  18. concentrationthe filtrate is concentrated to dryness under reduced pressure (20 mm Hg; 2.7 kPa) at 40° C

Sources & evidence

ORD record
ord-a7c493e207b742f39c5942d79e914a9b
Source dataset
uspto-grants-1986_06
Patent number
US04593101

Reaction notes

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