Iodine → 1-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclobutanol

HRID 340642Notes

Reaction equation

HRID 340642 reaction equation
[NH2:1][CH2:2][C:3]1([OH:7])[CH2:6][CH2:5][CH2:4]1.[CH3:8][C:9]([CH3:14])([CH3:13])[CH2:10][CH:11]=O.[S-:15][C:16]#[N:17].[K+].II>C(#N)C>[C:9]([C:10]1[S:15][C:16](=[NH:17])[N:1]([CH2:2][C:3]2([OH:7])[CH2:6][CH2:5][CH2:4]2)[CH:11]=1)([CH3:14])([CH3:13])[CH3:8]

Participants

6

Reactant 4

HCID 807IodineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 282600091-(Aminomethyl)cyclobutan-1-ol

Product 1

HCID 668520141-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclobutanolYield 32.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(aminomethyl)cyclobutanol (prepared from cyclobutanone as described in WO 2006/100208) (7.2 g, 71 mmol), 3,3-dimethylbutanal (9.8 mL, 78 mmol), 4 Å molecular sieves (10 g, 8-12 mesh beads), potassium thiocyanate (9.2 g, 95 mmol) and iodine (18 g, 71 mmol) in acetonitrile (100 mL) were processed as described in Example 1A to provide the title compound (5.5 g, 23 mmol, 32% yield). MS (DCI/NH3) m/z 241 (M+H)+.

Sources & evidence

ORD record
ord-6a57dff3764b4b959afb1e9b0216f1c8
Source dataset
uspto-grants-2014_11
Patent number
US08895592B2

Reaction notes

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