Potassium Carbonate → 4-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonate

HRID 2258264Notes

Reaction equation

HRID 2258264 reaction equation
Cl.[N+:2]([C:5]1[CH:20]=[CH:19][C:8]([O:9][C:10]([O:12][CH2:13][C:14]2[S:18][CH:17]=[N:16][CH:15]=2)=[O:11])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])[O-].[K+].[K+]>C(OCC)(=O)C>[N+:2]([C:5]1[CH:6]=[CH:7][C:8]([O:9][C:10]([O:12][CH2:13][C:14]2[S:18][CH:17]=[N:16][CH:15]=2)=[O:11])=[CH:19][CH:20]=1)([O-:4])=[O:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 218783405-Hydroxymethylthiazole 4-nitrophenylcarbonate hydrochloride

Product 1

HCID 98821474-Nitrophenyl 1,3-thiazol-5-ylmethyl carbonateYield 93.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

5-(p-Nitrophenoxycarbonyloxymethyl)thiazole hydrochloride (3.0 g) was slurried in ethyl acetate (30 mL) and cooled to 10°-15° C. A solution of 5% aqueous potassium carbonate (30 mL) was added with rapid stirring. After 15 minutes, stirring was stopped and the aqueous layer was separated. The organic layer was dried with Na2SO4 (3 g), filtered, and solvent was distilled under vacuum to give 2.49 g of the title compound as a brown syrup which slowly solidified, m.p. 62°-64° C. 1H NMR (CDCl3) δ8.90 (d, 1H), 8.29 (m, 2H), 8.01 (d, 1H), 7.39 (m, 2H), 5.52 (s, 2H). 13C NMR (CDCl3) δ155.4, 155.2, 152.2, 145.4, 144.9, 130.6, 125.3, 121.6, 61.9.

Workup

  1. temperaturecooled to 10°-15° C
  2. customthe aqueous layer was separated
  3. dry with materialThe organic layer was dried with Na2SO4 (3 g)
  4. filtrationfiltered
  5. distillationsolvent was distilled under vacuum

Sources & evidence

ORD record
ord-936e04b4156d4fddb5ad1a33f396de1d
Source dataset
uspto-grants-1997_08
Patent number
US05659045

Reaction notes

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