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

HRID 1419337Notes

Reaction equation

HRID 1419337 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) 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. 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-e3faa6c89e404dba9f352257a0e63cd8
Source dataset
uspto-grants-1999_03
Patent number
US05886036

Reaction notes

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