Trifluoroacetic acid → HCID 178476695, compound

HRID 444560Notes

Reaction equation

HRID 444560 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 16.5 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 was added dropwise. The mixture were 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 washed well with n-hexane ad the n-hexane was discarded after 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 were 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. washThe product was washed well with n-hexane ad the n-hexane
  7. customafter being removed by decantation
  8. additionTo the oily residue was added ether
  9. customwhereupon a crystalline powder separated out
  10. additionthe addition of a small amount of ether
  11. filtrationthe crystalline powder was collected by filtration
  12. washwashed with a small amount of ether
  13. customdried

Sources & evidence

ORD record
ord-b2582523aed54092a035a669735dc37e
Source dataset
uspto-grants-1981_04
Patent number
US04264595

Reaction notes

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