Hydrochloric Acid → Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

HRID 261986Notes

Reaction equation

HRID 261986 reaction equation
[C:1](Cl)([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.[NH2:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:33][OH:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=1.CN(C)C=O.Cl>O.C(N(CC)CC)C>[C:1]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:33][OH:34])[C:28]([O:30][CH2:31][CH3:32])=[O:29])[N:26]=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

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 6456Trityl chlorideHCID 6738988Ethyl 2-(2-aminothiazole-4-yl)-2-hydroxyiminoacetate

Product 1

HCID 6802348Ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoacetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

47.6 g of trityl chloride were added in small portions over 30 minutes to a mixture (cooled at -30° C.) of 32.2 g of the anti isomer of ethyl 2-(2-amino-4-thiazolyl)-2-hydroxyiminoacetate of Step A of Example 1, 90 ml of dry dimethylformamide and 24 ml of triethylamine and the mixture was left to spontaneous heating for 2 1/2 hours. Then, 150 ml of 2N hydrochloric acid and 600 ml of water were added thereto and the mixture was stirred for 15 minutes, then vacuum filtered. The recovered precipitate was empasted 3 times with ether and was then taken up in a mixture of methanol, water and triethylamine. The mixture was stirred and the vacuum filtered. The recovered product was rinsed with aqueous methanol and dried to obtain 60.2 g of the anti isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoaetate. 3.4 g of the said product were recrystallized from a methylene chloride-methanol mixture to obtain 3 g of pure product melting at 260° C.

Workup

  1. waitthe mixture was left
  2. temperatureto spontaneous heating for 2 1/2 hours
  3. filtrationvacuum filtered
  4. additionwas then taken up in a mixture of methanol, water and triethylamine
  5. stirringThe mixture was stirred
  6. filtrationthe vacuum filtered
  7. washThe recovered product was rinsed with aqueous methanol
  8. customdried
  9. customto obtain 60.2 g of the anti isomer of ethyl 2-(2-tritylamino-4-thiazolyl)-2-hydroxyiminoaetate
  10. custom3.4 g of the said product were recrystallized from a methylene chloride-methanol mixture

Sources & evidence

ORD record
ord-1fa40e70b449422eb6a4d4f3817b361c
Source dataset
uspto-grants-1979_05
Patent number
US04152432

Reaction notes

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