Morpholine → 4-(4-Chlorothiazol-2-YL)morpholine

HRID 1660746Notes

Reaction equation

HRID 1660746 reaction equation
Cl[C:2]1[S:3][CH:4]=[C:5]([Cl:7])[N:6]=1.C(=O)([O-])[O-].[K+].[K+].[NH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1>C(#N)C>[Cl:7][C:5]1[N:6]=[C:2]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[S:3][CH:4]=1

Participants

5

Reactant 3

HCID 8083MorpholineHCID 11430Potassium CarbonateHCID 123331552,4-Dichlorothiazole

Product 1

HCID 534400954-(4-Chlorothiazol-2-YL)morpholineYield 76.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

To a mixture of 2,4-dichlorothiazole (34 g, 0.22 mol) in acetonitrile (425 mL) add potassium carbonate (60.9 g, 0.44 mol) and then morpholine (21.2 mL, 0.225 mol) dropwise over 30 min. Reflux the mixture at 40° C. and then cool to 22° C. Filter the mixture and evaporate the filtrate. Triturate the residue with i-propyl alcohol (60 mL) at 22° C. for one hour. Filter the solids and dry under vacuum to a constant weight to afford the title compound (34.5 g, 76%). ES/MS m/z (35Cl) 205 (M+1)+.

Workup

  1. temperaturecool to 22° C
  2. filtrationFilter the mixture
  3. customevaporate the filtrate
  4. customTriturate the residue with i-propyl alcohol (60 mL) at 22° C. for one hour
  5. filtrationFilter the solids
  6. customdry under vacuum to a constant weight

Sources & evidence

ORD record
ord-08d5677c8a3242859bf8f53f6d34813b
Source dataset
uspto-grants-2011_10
Patent number
US08030304B2

Reaction notes

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