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

HRID 1010225Notes

Reaction equation

HRID 1010225 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 brine 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 brine
  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-1166bce1da594aab9b0ba59fc290ccd6
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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