2-Aminothiazole → HCID 686488, compound

HRID 2109429Notes

Reaction equation

HRID 2109429 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.C(N(CC)CC)C.Cl[C:15]([O:17][CH3:18])=[O:16]>CN(C1C=CN=CC=1)C.O1CCCC1>[S:3]1[CH:4]=[CH:5][N:6]=[C:2]1[NH:1][C:15](=[O:16])[O:17][CH3:18]

Participants

6

Reactant 3

HCID 21552-AminothiazoleHCID 6586Methyl chloroformateHCID 8471Triethylamine

Product 1

HCID 686488HCID 686488, compoundYield 107.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Aminothiazole (10.00 g, 99.86 mmole), triethylamine (20.2 g, 200 mmol) and a catalytic amount of 4-(N,N-dimethylamino)pyridine in anhydrous tetrahydrofuran (200 mL) were stirred at 0° C. Methyl chloroformate (18.9 g, 200 mmol) was added slowly to the mixture at 0° C. Then the reaction mixture was stirred at room temperature for several hours. The tetrahydrofuran was evaporated, the residue was dissolved in chloroform, and the resulting solution was washed with water, dried through magnesium sulfate, filtered, and then the solvent was evaporated. The residue was purified by flash chromatography using a gradient of ammoniated methanol in chloroform to give the sub-title compound as a pale yellow solid (17.0 g), m/z 159 (MH+).

Workup

  1. customThe tetrahydrofuran was evaporated
  2. dissolutionthe residue was dissolved in chloroform
  3. washthe resulting solution was washed with water
  4. dry with materialdried through magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-04cecd74d9a24ef395d536c667252b0b
Source dataset
uspto-grants-2009_04
Patent number
US07514567B2

Reaction notes

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