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

HRID 254633Notes

Reaction equation

HRID 254633 reaction equation
[NH2:1][CH2:2][C:3]1([OH:6])[CH2:5][CH2:4]1.[CH3:7][C:8]([CH3:13])([CH3:12])[CH2:9][CH:10]=O.[S-:14][C:15]#[N:16].[K+].II>C(#N)C>[C:8]([C:9]1[S:14][C:15](=[NH:16])[N:1]([CH2:2][C:3]2([OH:6])[CH2:5][CH2:4]2)[CH:10]=1)([CH3:13])([CH3:12])[CH3:7]

Participants

6

Reactant 4

HCID 807IodineHCID 763353,3-DimethylbutanalHCID 516872Potassium thiocyanateHCID 126096231-(Aminomethyl)cyclopropan-1-ol

Product 1

HCID 668519251-((5-tert-butyl-2-iminothiazol-3(2H)-yl)methyl)cyclopropanolYield 95.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 1-(aminomethyl)cyclopropanol (ChemPacific, 1.0 g, 11.5 mmol), 3,3-dimethylbutanal (1.6 mL, 12.6 mmol), 4 Å molecular sieves (3 g, 8-12 mesh beads), potassium thiocyanate (1.5 g, 15 mmol) and iodine (2.9 g, 11.5 mmol) in acetonitrile (25 mL) were processed as described in Example 18A to provide the title compound (2.5 g, 11 mmol, 95% yield). MS (DCI/NH3) m/z 227 (M+H)+.

Sources & evidence

ORD record
ord-3b6347423f744a38a8c49fdd9e99d6a4
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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