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

HRID 387838Notes

Reaction equation

HRID 387838 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(OCC)(=O)C.O1CCCC1>CN(C)C=O.O>[C:17]1([O:16][C:14](=[O:15])[NH:1][C:2]2[S:3][CH:4]=[CH:5][N:6]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 1049PyridineHCID 21552-AminothiazoleHCID 15891Phenyl chloroformateHCID 21939870Tetrahydrofuran ethyl acetate

Product 1

HCID 651148phenyl N-(1,3-thiazol-2-yl)carbamateYield 96.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving 2-aminothiazole (5.01 g, 50.0 mmol) and pyridine (7.91 g, 100 mmol) in dimethylformamide (50 ml), phenyl chloroformate (8.22 g, 52.5 mmol) was added while cooling on ice, and the mixture was stirred at room temperature for 1 hour. The reaction solution was distributed between an ethyl acetate-tetrahydrofuran mixed solvent and water, the organic layer was washed with water and saturated saline and dried over anhydrous magnesium sulfate, the drying agent was filtered off and the filtrate was distilled off under reduced pressure. After adding ethyl acetate and then hexane to the obtained crude product, the precipitated crystals were filtered out and blow-dried to obtain the title compound (10.6 g, 48.1 mmol, 96%) as colorless crystals.

Workup

  1. additionwas added
  2. temperaturewhile cooling on ice
  3. washthe organic layer was washed with water and saturated saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationthe drying agent was filtered off
  6. distillationthe filtrate was distilled off under reduced pressure
  7. additionAfter adding ethyl acetate
  8. customhexane to the obtained crude product
  9. filtrationthe precipitated crystals were filtered out and
  10. customblow-dried

Sources & evidence

ORD record
ord-c10ee5aea83942f1ab6016b659ed1891
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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