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

HRID 538774Notes

Reaction equation

HRID 538774 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-69a917923d6e44ed966992dd566e2edc
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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