Morpholine → 4-Bromo-2-morpholinothiazole-5-sulfonamide

HRID 2402135Notes

Reaction equation

HRID 2402135 reaction equation
Br[C:2]1[S:3][C:4]([S:8]([NH2:11])(=[O:10])=[O:9])=[C:5]([Br:7])[N:6]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1COCC1>[Br:7][C:5]1[N:6]=[C:2]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[S:3][C:4]=1[S:8]([NH2:11])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 8083MorpholineHCID 10796Cesium carbonateHCID 667482872,4-Dibromothiazole-5-sulfonamide

Product 1

HCID 667475964-Bromo-2-morpholinothiazole-5-sulfonamideYield 44%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2,4-dibromothiazole-5-sulfonamide (0.515 g, 1.60 mmol), morpholine (0.153 mL, 1.76 mmol), THF (4.22 mL) and cesium carbonate (1.56 g, 4.80 mmol) in a sealed tube was heated to 80 degrees for 4 hours. The cooled reaction was concentrated in vacuo and the residue was taken up in ethyl acetate (50 mL) and water (25 mL). The layers were separated and the organic layer was washed with water (15 mL), dried and concentrated in vacuo. The residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→50/50) to give 230 mg (44% yield) of the title compound as a white solid. LC/MS (FA) ES+ 328, 330. 1H NMR (400 MHz, DMSO-d6) δ: 7.76 (s, 2H), 3.69-3.66 (m, 4H), 3.43-3.40 (m, 4H).

Workup

  1. temperaturewas heated to 80 degrees for 4 hours
  2. customThe cooled reaction
  3. concentrationwas concentrated in vacuo
  4. customThe layers were separated
  5. washthe organic layer was washed with water (15 mL)
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by silica gel chromatography (ethyl acetate/DCM=0/100→50/50)

Sources & evidence

ORD record
ord-ba7f6224d8d34f5d9189f55508154e83
Source dataset
uspto-grants-2014_08
Patent number
US08796271B2

Reaction notes

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