Iodine → 3-(cyclobutylmethyl)-4,4,6,6-tetramethyl-4,6-dihydrofuro[3,4-d]thiazol-2(3H)-imine

HRID 538818Notes

Reaction equation

HRID 538818 reaction equation
[CH3:1][C:2]1([CH3:10])[C:6](=O)[CH2:5][C:4]([CH3:9])([CH3:8])[O:3]1.Cl.[CH:12]1([CH2:16][NH2:17])[CH2:15][CH2:14][CH2:13]1.[S-:18][C:19]#[N:20].[K+].II>C(N(CC)CC)C>[CH:12]1([CH2:16][N:17]2[C:5]3[C:4]([CH3:9])([CH3:8])[O:3][C:2]([CH3:10])([CH3:1])[C:6]=3[S:18][C:19]2=[NH:20])[CH2:15][CH2:14][CH2:13]1

Participants

6

Reactant 4

HCID 807IodineHCID 1385112,2,5,5-Tetramethyltetrahydro-3-ketofuranHCID 516872Potassium thiocyanateHCID 217079441-Cyclobutylmethanamine hydrochloride

Product 1

HCID 668521273-(cyclobutylmethyl)-4,4,6,6-tetramethyl-4,6-dihydrofuro[3,4-d]thiazol-2(3H)-imine

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Commercially available 2,2,5,5-tetramethyldihydrofuran-3(2H)-one (Aldrich), triethylamine, cyclobutylmethanamine hydrochloride (prepared from cyclobutanecarbonitrile as described in WO2005075464), potassium thiocyanate (Aldrich) and iodine (EMD chemicals) were processed using the method described in Example 91A to afford the title compound. MS (ESI+) m/z 267 (M+H)+

Sources & evidence

ORD record
ord-44a66e020e7c49528cc3d8f648fb4ad7
Source dataset
uspto-grants-2014_10
Patent number
US08865753B2

Reaction notes

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