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

HRID 254677Notes

Reaction equation

HRID 254677 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-5920738ea4e24b7aad59752f8268b4db
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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