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

HRID 42792

Reaction equation

HRID 42792 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](=O)[CH2:14]Cl.CCOC(C)=O>C1(C)C=CC=CC=1>[CH2:3]([O:5][C:6]([C:7]1[S:8][CH:14]=[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 mixture of amino-thioxo-acetic acid ethyl ester (2.50 g, 18.77 mmol) and 1,3-dichloro-propan-2-one (2.88 g, 21.59 mmol) in toluene (20.0 mL) was stirred for 2 h at reflux. EtOAc (20 mL) was added at rt and the mixture was washed with sat. aq. NaHCO3 (10 mL) followed by brine (20 mL). The organic layer was dried over MgSO4, filtered, and the solvent removed under reduced pressure. Purification of the residue by FC (4:1 hept-EA) gave the title compound as a light yellow oil. TLC:rf (4:1 hept-EA)=0.26. LC-MS-conditions 02: tR=0.89 min, [M+H]+=206.40.

Workup

  1. temperatureat reflux
  2. washthe mixture was washed with sat. aq. NaHCO3 (10 mL)
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customPurification of the residue by FC (4:1 hept-EA)

Sources & evidence

ORD record
ord-494ac4085b1b412d9895b560863ddcf1
Source dataset
uspto-grants-2013_09
Patent number
US08536209B2

Linked notes

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