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

HRID 254641Notes

Reaction equation

HRID 254641 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-enyl-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-7a5c4554b89e4ff297486e9ea118ba27
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

Loading…