Iodine → 5-tert-butyl-3-(3-methylbut-2-enyl)thiazol-2(3H)-imine

HRID 538782Notes

Reaction equation

HRID 538782 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[CH2:3][CH:4]=O.Cl.[CH3:9][C:10]([CH3:14])=[CH:11][CH2:12][NH2:13].C(N(CC)CC)C.[C:22]([S-:24])#[N:23].[K+].II>CC#N>[C:2]([C:3]1[S:24][C:22](=[NH:23])[N:13]([CH2:12][CH:11]=[C:10]([CH3:14])[CH3:9])[CH:4]=1)([CH3:7])([CH3:6])[CH3:1]

Participants

7

Reactant 5

HCID 807IodineHCID 8471TriethylamineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 183265643-Methylbut-2-en-1-amine hydrochloride

Product 1

HCID 668524175-tert-butyl-3-(3-methylbut-2-enyl)thiazol-2(3H)-imine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3,3-Dimethylbutanal (0.95 g, 9.1 mmol), 3-methylbut-2-en-1-amine hydrochloride (1.1 g, 9.1 mmol), and triethylamine (1.3 mL, 9.1 mmol) were mixed in 9 mL of dry MeCN with 2 g of 4 Å (8-12 mesh beads) molecular sieves and stirred for 20 hours at room temperature. The reaction was filtered through Celite and washed with 8 mL of MeCN. KSCN (1.2 g, 12.3 mmol) was added and the mixture warmed to 50° C. Iodine (2.3 g, 9.1 mmol) was added and the reaction stirred at 50° C. for 6 hours. 20% Na2S2O5 was added, stirred for 30 minutes and the organic layer separated, dried with Na2SO4 and the solvent removed. The resulting solid was used without further purification. LC/MS m/z 225.3 (M+H)+.

Workup

  1. filtrationThe reaction was filtered through Celite
  2. washwashed with 8 mL of MeCN
  3. temperaturethe mixture warmed to 50° C
  4. stirringthe reaction stirred at 50° C. for 6 hours
  5. stirringstirred for 30 minutes
  6. customthe organic layer separated
  7. dry with materialdried with Na2SO4
  8. customthe solvent removed
  9. customThe resulting solid was used without further purification

Sources & evidence

ORD record
ord-6a91e3958e8345c4a415d1f4e7900dc7
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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