Morpholine → HCID 1490754, compound

HRID 1890765Notes

Reaction equation

HRID 1890765 reaction equation
Cl[C:2]1[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>CS(C)=O>[O:19]1[CH2:20][CH2:21][N:16]([C:2]2[S:3][C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]([C:7]([F:10])([F:9])[F:8])[N:6]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 1235240Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate

Product 1

HCID 1490754HCID 1490754, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Add ethyl 2-chloro-4-(trifluoromethyl)thiazole-5-carboxylate (4.00 g, 15.4 mmol) to a solution of morpholine (4.03 g, 46.2 mmol) in DMSO (10 mL). Stir the reaction at ambient temperature overnight. Add CH2Cl2, and wash the mixture with H2O. Dry the organic phase over Na2SO4, filter, and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (20:5:1 hexanes:EtOAc:2 M NH3/MeOH) to yield the title compound (4.58 g, 96%). ES/MS m/z 311.0 (M+1).

Workup

  1. customthe reaction at ambient temperature overnight
  2. washAdd CH2Cl2, and wash the mixture with H2O
  3. dry with materialDry the organic phase over Na2SO4
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure
  6. customPurify the resulting residue by flash silica gel chromatography (20:5:1 hexanes:EtOAc:2 M NH3/MeOH)

Sources & evidence

ORD record
ord-4b980fa5ea794ad3978ef81551eab22e
Source dataset
uspto-grants-2013_08
Patent number
US08507490B2

Reaction notes

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