Pyridine → phenyl N-(1,3-thiazol-2-yl)carbamate

HRID 218177

Reaction equation

HRID 218177 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.N1C=CC=CC=1.Cl[C:14]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:15].C(=O)(O)[O-].[Na+]>ClCCl>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:14](=[O:15])[O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 15891Phenyl chloroformateHCID 516892Sodium Bicarbonate

Product 1

HCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of 2-aminothiazole (2 g, 20 mmol), pyridine (10 mL), and anhydrous dichloromethane (20 mL) was added phenyl chloroformate (3 mL, 24 mmol) under argon at 0° C. The mixture was stirred at the same temperature for 5 min and at rt overnight before saturated aqueous sodium bicarbonate solution (30 mL) was added slowly. After mixed with heptanes (30 mL), the mixture was stirred for 30 min. The solid was filtered, washed with water (3×3 mL) and then diethylether (3×3 mL), and dried to give phenyl thiazol-2-ylcarbamate (3.4 g, 15 mmol, 75% yield) as an off-white solid.

Workup

  1. additionwas added slowly
  2. filtrationThe solid was filtered
  3. washwashed with water (3×3 mL)
  4. dry with materialdiethylether (3×3 mL), and dried

Sources & evidence

ORD record
ord-55cb337be6a64da6b0ebcb892d442c5e
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Linked notes

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