Trityl chloride → HCID 11733186, compound

HRID 2107844Notes

Reaction equation

HRID 2107844 reaction equation
[H-].[Na+].[NH2:3][C:4]1[S:5][CH:6]=[C:7](/[C:9](=[N:15]/[OH:16])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1.[C:17](Cl)([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C1COCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7](/[C:9](=[N:15]/[O:16][C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 6456Trityl chlorideHCID 24758Sodium hydrideHCID 6401018Ethyl 2-amino-alpha-(hydroxyimino)thiazol-4-acetate

Product 1

HCID 11733186HCID 11733186, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium hydride (60% dispersion in mineral oil, 13.2 g, 0.33 mol) was added portionwise to a cold (0° C.) mixture of ethyl (Z)-(2-aminothiazol-4-yl)-2-hydroxyiminoacetate (64.5 g, 0.3 mol) in dry THF (1 L) with vigorous stirring and the mixture was stirred for 0.5 hr. at room temperature. To the mixture was added a solution of trityl chloride (92.0 g, 0.33 mol) in dry THF (0.2 L) with cooling and stirring. The mixture was stirred for 2 hr. at ambient temperature and evaporated under reduced pressure. Chloroform (1 L) was added to the residue and the mixture was washed with water. The insoluble material was filtered and the organic layer of the filtrate was separated. The insoluble material was extracted again with a mixture of chloroform (300 ml) and methanol (50 ml) by sonication for 10 min. and subsequent filtration. The extract was combined with the separated organic layer and evaporated under reduced pressure. The residue was triturated with toluene (0.3 L) to crystallize the product as colorless prisms, which were collected by filtration, washed with a small toluene and dried in vacuo. Yield, 91.2 g (66%). The filtrate was evaporated and treated with toluene to give 19.2 g of the second crop.

Workup

  1. stirringthe mixture was stirred for 0.5 hr
  2. customat room temperature
  3. temperaturewith cooling
  4. stirringstirring
  5. stirringThe mixture was stirred for 2 hr
  6. customat ambient temperature and evaporated under reduced pressure
  7. additionChloroform (1 L) was added to the residue
  8. washthe mixture was washed with water
  9. filtrationThe insoluble material was filtered
  10. customthe organic layer of the filtrate was separated
  11. extractionThe insoluble material was extracted again with a mixture of chloroform (300 ml) and methanol (50 ml) by sonication for 10 min.
  12. filtrationsubsequent filtration
  13. customevaporated under reduced pressure
  14. customThe residue was triturated with toluene (0.3 L)
  15. customto crystallize the product as colorless prisms, which
  16. filtrationwere collected by filtration
  17. washwashed with a small toluene
  18. customdried in vacuo
  19. customYield
  20. customThe filtrate was evaporated
  21. additiontreated with toluene
  22. customto give 19.2 g of the second crop

Sources & evidence

ORD record
ord-585ec264400e4f578d83a26921937ef1
Source dataset
uspto-grants-1990_06
Patent number
US04935508

Reaction notes

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