Iodine → 3-tert-Butyl-1,2-thiazol-5-amine

HRID 469764Notes

Reaction equation

HRID 469764 reaction equation
[NH2:1]/[C:2](/[C:7]([CH3:10])([CH3:9])[CH3:8])=[CH:3]\[C:4](=[S:6])[NH2:5].C(=O)([O-])[O-].[K+].[K+].II.O>C(OCC)C>[C:7]([C:2]1[CH:3]=[C:4]([NH2:5])[S:6][N:1]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 807IodineHCID 962WaterHCID 11430Potassium CarbonateHCID 21812870HCID 21812870, compound

Product 1

HCID 151170133-tert-Butyl-1,2-thiazol-5-amineYield 53%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred solution of (Z)-3-amino-4,4-dimethyl-pent-2-enethioic acid amide (8.3 g, 525 mmol) and potassium carbonate (14.4 g, 105 mmol) in 140 mL of diethyl ether is added a solution of iodine (13.2 g, 52.5 mmol) in 20 mL of diethyl ether at reflux. The mixture is refluxed for 2 h and cooled. Water is added and the layers separated. The organic layer is washed with water, dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude mixture is purified by flash chromatography to afford title compound in 53% yield. ESI m/z 157=MH+

Workup

  1. temperatureat reflux
  2. temperatureThe mixture is refluxed for 2 h
  3. temperaturecooled
  4. customthe layers separated
  5. washThe organic layer is washed with water
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude mixture is purified by flash chromatography

Sources & evidence

ORD record
ord-645a3e4dff76486ea0323a44d40183d9
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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