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

HRID 850583Notes

Reaction equation

HRID 850583 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

Conditions

Temperature
12.5 °C

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) δ 8.90 (d, 1H), 8.29 (m, 2H), 8.01 (d, 1H), 7.39 (m, 2H), 5.52 (s, 2H). 13C NMR (CDCl3) δ 155.4, 155.2, 152.2, 145.4, 144.9, 130.6, 125.3, 121.6, 61.9.

Workup

  1. customthe aqueous layer was separated
  2. dry with materialThe organic layer was dried with Na2SO4 (3 g)
  3. filtrationfiltered
  4. distillationsolvent was distilled under vacuum

Sources & evidence

ORD record
ord-c85fa6345dc1427caed9ea40a3673b60
Source dataset
uspto-grants-2000_01
Patent number
US06017928

Reaction notes

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