Hydrochloric Acid → HCID 53889719, compound

HRID 851823Notes

Reaction equation

HRID 851823 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][OH:31])[C:27]([OH:29])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:32](=O)([O-])[O-].[K+].[K+].Cl[CH2:39][C:40]#[N:41].Cl.C[N:44]([CH3:47])C=O>C(OCC)(=O)C.O>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH2:32][C:47]#[N:44])[C:27]([O:29][CH2:39][C:40]#[N:41])=[O:28])[N:25]=1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 7856ChloroacetonitrileHCID 11430Potassium CarbonateHCID 730781342-(2-Tritylamino-4-thiazolyl)-2-hydroxyimino-acetic acid

Product 1

HCID 53889719HCID 53889719, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 12.9 g of the syn isomer of 2-(2-tritylamino-4-thiazolyl)-2-hydroxyimino-acetic acid, 9.12 g of neutral potassium carbonate, 60 ml of dry dimethylformamide and 7.6 ml of chloroacetonitrile was stirred under an inert atmosphere and after formation of a mass, the mixture stood for 65 hours under a closed atmosphere. The product was poured into a mixture of 750 ml of water, 130 ml of N hydrochloric acid and 150 ml of ethyl acetate and the mixture was stirred and vacuum filtered. The filter was rinsed with ethyl acetate and with water and the filtrate was decanted. The organic phase was washed with 100 ml of water and the aqueous phase was extracted 3 times with 100 ml of ethyl acetate. The combined organic phases were dried and were vacuum filtered. The filter was rinsed and the filtrate was evaporated to dryness and the residue was chromatographed over silica gel. Elution with ether yielded 8.69 g of the syn isomer of cyanomethyl 2-(2-tritylamino- 4-thiazolyl)-2-cyanomethyloxyimino-acetate in the form of an oil.

Workup

  1. stirringthe mixture was stirred
  2. filtrationvacuum filtered
  3. washThe filter was rinsed with ethyl acetate and with water
  4. customthe filtrate was decanted
  5. washThe organic phase was washed with 100 ml of water
  6. extractionthe aqueous phase was extracted 3 times with 100 ml of ethyl acetate
  7. customThe combined organic phases were dried
  8. filtrationfiltered
  9. washThe filter was rinsed
  10. customthe filtrate was evaporated to dryness
  11. customthe residue was chromatographed over silica gel
  12. washElution with ether

Sources & evidence

ORD record
ord-0c51d33af5184e80a10dc3ef6c936675
Source dataset
uspto-grants-1983_05
Patent number
US04386210

Reaction notes

Loading…