Nitrogen → Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

HRID 2065019Notes

Reaction equation

HRID 2065019 reaction equation
N#N.[CH2:3]([O:5][C:6](=[O:10])[C:7]([NH2:9])=[S:8])[CH3:4].[Cl:11][CH2:12][C:13]([CH2:15]Cl)=O.CC(=O)OCC>C1(C)C=CC=CC=1>[CH2:3]([O:5][C:6]([C:7]1[S:8][CH:15]=[C:13]([CH2:12][Cl:11])[N:9]=1)=[O:10])[CH3:4]

Participants

6

Reactant 4

HCID 947NitrogenHCID 8857Ethyl AcetateHCID 107931,3-DichloroacetoneHCID 2733398Ethyl thiooxamate

Product 1

HCID 10822129Ethyl 4-(chloromethyl)-1,3-thiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of amino-thioxo-acetic acid ethyl ester (2.03 g. 15.27 mmol) in toluene (16.7 mL) was treated with 1,3-dichloroacetone (2.22 g, 17.50 mmol). The resulting mixture was stirred at reflux for 2 h. EA (20 mL) was added and the org. layer was washed with sat. aq. NaHCO3, brine, dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the residue by FC (70:30 hept-EA) gave the title compound as an orange oil. TLC: rf (70:30 hept-EA)=0.40. LC-MS-conditions 02: tR=0.88 min; [M+H]+=206.37.

Workup

  1. temperatureat reflux for 2 h
  2. washlayer was washed with sat. aq. NaHCO3, brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customthe solvents were removed under reduced pressure
  6. customPurification of the residue by FC (70:30 hept-EA)

Sources & evidence

ORD record
ord-20c1491c378c41058a2b94c7d72c4faf
Source dataset
uspto-grants-2012_10
Patent number
US08288419B2

Reaction notes

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