Potassium Hydroxide → HCID 54571402, compound

HRID 2049172Notes

Reaction equation

HRID 2049172 reaction equation
[OH-].[K+].[C:3]([NH:22][C:23]1[S:24][CH:25]=[C:26]([C:28](=[N:34][O:35][CH:36]=[CH2:37])[C:29]([O:31]CC)=[O:30])[N:27]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[K]>C(O)C.O1CCOCC1>[C:3]([NH:22][C:23]1[S:24][CH:25]=[C:26]([C:28](=[N:34][O:35][CH:36]=[CH2:37])[C:29]([OH:31])=[O:30])[N:27]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 5462222PotassiumHCID 53851199HCID 53851199, compound

Product 1

HCID 54571402HCID 54571402, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
20 °C

Procedure

20 ml of a solution of 0.5 M of potassium hydroxide in absolute ethanol and 12 ml of absolute ethanol were added at room temperature to a mixture of 3.227 g of the product of Step D in 3.2 ml of dioxane and the mixture was stirred at 50° C. under argon for 1 hour during which a potassium salt crystallized. The mixture cooled to 20° C. and was vacuum filtered and the recovered product was rinsed with ethanol and was taken up in a mixture of 50 ml of ethyl acetate and 50 ml of distilled water. The mixture was acidified with 6 ml of 2 N hydrochloric acid and was stirred until 2 homogeous phases were obtained. The organic phase was decanted and was washed 3 times with 20 ml of distilled water. The wash waters were extracted with ethyl acetate and the combined organic phases were dried and vacuum filtered. The filter was rinsed with ethyl acetate and the filtrate was concentrated to a volume of 15 ml and was iced at 0° to 5° C. The mixture was vacuum filtered and the recovered product was rinsed with ethyl acetate and dried to obtain 2.53 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-vinyloxyiminoacetic acid which was used as is for the next step. A sample after crystallization melted at 150° C.

Workup

  1. customcrystallized
  2. filtrationfiltered
  3. washthe recovered product was rinsed with ethanol
  4. additionwas taken up in a mixture of 50 ml of ethyl acetate and 50 ml of distilled water
  5. customwere obtained
  6. customThe organic phase was decanted
  7. washwas washed 3 times with 20 ml of distilled water
  8. extractionThe wash waters were extracted with ethyl acetate
  9. customthe combined organic phases were dried
  10. filtrationvacuum filtered
  11. washThe filter was rinsed with ethyl acetate
  12. concentrationthe filtrate was concentrated to a volume of 15 ml
  13. customwas iced at 0° to 5° C
  14. filtrationfiltered
  15. washthe recovered product was rinsed with ethyl acetate
  16. customdried

Sources & evidence

ORD record
ord-8eb0c75b23234775819d2e63896c35e7
Source dataset
uspto-grants-1980_04
Patent number
US04196205

Reaction notes

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