Triethylamine → 2-(4-Morpholinylcarbonyl)-1,3-thiazol-5-amine

HRID 411208

Reaction equation

HRID 411208 reaction equation
[N:1]1([C:7](=[O:12])[C:8]([S:10][CH3:11])=S)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.S(=O)(=O)(O)O.[NH2:18][CH2:19]C#N.C([N:24](CC)CC)C>CO>[N:1]1([C:7]([C:8]2[S:10][C:11]([NH2:24])=[CH:19][N:18]=2)=[O:12])[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 196971Aminoacetonitrile sulfate (1:1)HCID 22397235Methyl 4-morpholinyl(oxo)ethanedithioate

Product 1

HCID 223972262-(4-Morpholinylcarbonyl)-1,3-thiazol-5-amineYield 31%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirring mixture of methyl 4-morpholinyl(oxo)ethanedithioate (Preparation 25, 500 mg) and aminoacetonitrile bisulfate (564 mg) in MeOH (10 mL) at 0° C. is added triethylamine in MeOH (5 mL). The mixture is stirred overnight and allowed to warm to ambient temperature. The solution is filtered, and solvent removed from the filtrate. The residue is washed with water (15 mL) and extracted with EtOAc (3×20 mL), dried over MgSO4, and the solvent removed. The residue is purified by SiO2 flash column chromatography (eluent 3/1 EtOAc/hexane) to afford 161 mg (31%) of the title compound as a light brown solid. Physical characteristics: 1H NMR (CDCl3) δ 3.78, 4.35, 7.05; IR (diffuse reflectance) 3321, 3217, 2858, 1580, 1438, 1418, 1348, 1276, 1178, 1113, 1003, 834, 783, 731, 619 cm−1; MS (ESI+) m/z 214 (M+H)+. Anal. Found: C, 45.24; H, 5.33; N, 19.42.

Workup

  1. filtrationThe solution is filtered
  2. customsolvent removed from the filtrate
  3. washThe residue is washed with water (15 mL)
  4. extractionextracted with EtOAc (3×20 mL)
  5. dry with materialdried over MgSO4
  6. customthe solvent removed
  7. customThe residue is purified by SiO2 flash column chromatography (eluent 3/1 EtOAc/hexane)

Sources & evidence

ORD record
ord-dbe59273da13454c960eff6e2169e250
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Linked notes

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