Pyridine → 4-Nitrophenyl 1,3-thiazol-2-ylcarbamate

HRID 2351269Notes

Reaction equation

HRID 2351269 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][CH:6]=1)=[O:3].[NH2:14][C:15]1[S:16][CH:17]=[CH:18][N:19]=1.N1C=CC=CC=1>C(OCC)(=O)C>[N+:11]([C:8]1[CH:9]=[CH:10][C:5]([O:4][C:2]([NH:14][C:15]2[S:16][CH:17]=[CH:18][N:19]=2)=[O:3])=[CH:6][CH:7]=1)([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 1049PyridineHCID 21552-AminothiazoleHCID 821294-Nitrophenyl chloroformate

Product 1

HCID 156927894-Nitrophenyl 1,3-thiazol-2-ylcarbamate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of 4-nitrophenyl chloroformate, 5.04 g (25 mMole), in 25 ml of dry ethyl acetate was added dropwise to an ice cooled, stirred solution of 2-aminothiazole, 5.01 g (50 mMole) in dry ethyl acetate, 25 ml, and dry pyridine, 50 ml. The ice bath was removed as the reaction mixture became viscous. Stirring was continued at 22° C. for three hours. Ethyl acetate was added. The insolubles were filtered, rinsed with ethyl acetate, with water, with acetone, dried and recrystallized from acetone furnishing 3.55 g of 2-(4-nitrophenoxycarbonyl)aminothiazole, m.p 211°-212° C. dec, which was characterized by nuclear magnetic resonance, mass spectra, infrared spectra and elemental analyses.

Workup

  1. temperaturecooled
  2. customThe ice bath was removed as the reaction mixture
  3. additionEthyl acetate was added
  4. filtrationThe insolubles were filtered
  5. washrinsed with ethyl acetate, with water, with acetone
  6. customdried
  7. customrecrystallized from acetone furnishing 3.55 g of 2-(4-nitrophenoxycarbonyl)aminothiazole, m.p 211°-212° C. dec, which

Sources & evidence

ORD record
ord-68d24fad69394ff1aa9610ea71269b01
Source dataset
uspto-grants-1989_10
Patent number
US04873224

Reaction notes

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