Water → Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate

HRID 1905575Notes

Reaction equation

HRID 1905575 reaction equation
[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][OH:33])[C:27]([O:29][CH2:30][CH3:31])=[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:34](=O)([O-])[O-].[K+].[K+].O.C(O[CH2:45][CH3:46])(=O)C>CN(C)C=O.C(I)(C)C>[C:1]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:32][O:33][CH:45]([CH3:46])[CH3:34])[C:27]([O:29][CH2:30][CH3:31])=[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

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Product 1

HCID 54071115Ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6362Isopropyl iodideSolvent

Procedure

A mixture of 6.86 g of the anti isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate of Example 14, 3.51 g of potassium carbonate in 15 ml of dimethylformamide and 7.7 ml of isopropyl iodide was held under an argon atmosphere and stirring for 41/2 hours and then 250 ml of distilled water and 150 ml of ethyl acetate were added thereto with stirring. The mixture was decanted and the aqueous phase was washed with water and was extracted with ethyl acetate. The organic phase was dried, vacuum filtered and evaporated to dryness. The residue was taken up in ethanol and crystallization started after seeding. The mixture was vacuum filtered and the precipitate was rinsed with ethanol and empasted with petroleum ether to obtain 3.26 g of the anti isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-(1-methylethoxyimino)-acetate melting at 182° C.

Workup

  1. stirringwith stirring
  2. customThe mixture was decanted
  3. washthe aqueous phase was washed with water
  4. extractionwas extracted with ethyl acetate
  5. customThe organic phase was dried
  6. filtrationvacuum filtered
  7. customevaporated to dryness
  8. customcrystallization
  9. filtrationfiltered
  10. washthe precipitate was rinsed with ethanol

Sources & evidence

ORD record
ord-51ba15dd497e4a21aa893a8e5082f14f
Source dataset
uspto-grants-1989_06
Patent number
US04843164

Reaction notes

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