Trifluoroacetic acid → HCID 178476695, compound

HRID 1088659Notes

Reaction equation

HRID 1088659 reaction equation
[C:1]([O:4][N:5]=[C:6]([C:23]1[NH:24][C:25](=[N:28][C:29](=[O:32])[CH2:30][Cl:31])[S:26][CH:27]=1)[C:7]([O:9]C(C1C=CC=CC=1)C1C=CC=CC=1)=[O:8])(=[O:3])[CH3:2].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[C:1]([O:4][N:5]=[C:6]([C:23]1[NH:24][C:25](=[N:28][C:29](=[O:32])[CH2:30][Cl:31])[S:26][CH:27]=1)[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178476696HCID 178476696, compound

Product 1

HCID 178476695HCID 178476695, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

In 116.5 ml of anisole there were suspended 6.10 g of benzhydryl 2-acetoxyimino-2-(2-chloroacetylimino-4-thiazolin-4-yl)acetate(syn-isomer) and under ice-cooling and stirring, 65.7 ml of trifluoroacetic acid were added dropwise. The mixture was stirred at that temperature for 15 minutes, after which the trifluoroacetic acid was distilled off under reduced pressure. To the residue was added n-hexane, whereupon an oily product separated out. The product was wahsed well with n-hexane and the n-hexane was discarded ater being removed by decantation. This procedure was carried out once again. To the oily residue was added ether, whereupon a crystalline powder separated out. Following the addition of a small amount of ether, the crystalline powder was collected by filtration, washed with a small amount of ether and dried. By the above procedure there were obtained 3.125 g of 2-acetoxyimino-2-(2-chloroacetylimino-4-thiazolin-4-yl)acetic acid (syn-isomer).

Workup

  1. temperatureunder ice-cooling
  2. stirringThe mixture was stirred at that temperature for 15 minutes
  3. distillationafter which the trifluoroacetic acid was distilled off under reduced pressure
  4. additionTo the residue was added n-hexane
  5. customwhereupon an oily product separated out
  6. customater being removed by decantation
  7. additionTo the oily residue was added ether
  8. customwhereupon a crystalline powder separated out
  9. additionthe addition of a small amount of ether
  10. filtrationthe crystalline powder was collected by filtration
  11. washwashed with a small amount of ether
  12. customdried

Sources & evidence

ORD record
ord-854775dc98d44264b1024b19638ba0c8
Source dataset
uspto-grants-1990_10
Patent number
US04963542

Reaction notes

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