Water → 3,4-Dihydro-2-isoprenyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole

HRID 544357Notes

Reaction equation

HRID 544357 reaction equation
[OH:1][CH2:2][CH:3]1[S:15][C:7]2=[N:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]2[CH2:5][CH2:4]1.[H-].[Na+].[CH:18](Br)=[CH:19][C:20](=[CH2:22])[CH3:21].O>O1CCCC1>[CH:18]([O:1][CH2:2][CH:3]1[S:15][C:7]2=[N:8][C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[N:6]2[CH2:5][CH2:4]1)=[CH:19][C:20](=[CH2:21])[CH3:22]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 128523233,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleHCID 53976308Bromoisoprene

Product 1

HCID 867387543,4-Dihydro-2-isoprenyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazoleYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of one gram of 3,4-dihydro-2-hydroxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole in dry tetrahydrofuran (20 ml) was treated with 0.5 g of 50% sodium hydride containing mineral oil at 0° C. under stirring. The mixture was stirred for 1 hr, then one gram of isoprenylbromide was added, and the stirring was continued for three hours at room temperature. The reaction mixture was condensed under reduced pressure. The residue was added with water and then extracted with chloroform, and dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 0.42 g (yield: 30%) of the intended product, m.p. 56°-60° C.; IR νmaxKBr cm-1 : 3100-2850, 1600, 1420; Anal. Calcd. for C16H20N2OS: C, 66.63; H, 6.99; N, 9.71; S, 11.12; Found: C, 66.64; H, 6.92; N, 9.94; S, 10.89.

Workup

  1. stirringThe mixture was stirred for 1 hr
  2. customcondensed under reduced pressure
  3. extractionextracted with chloroform
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customChloroform was evaporated under reduced pressure
  6. customThe residue was chromatographed on silica gel
  7. washeluted with chloroform

Sources & evidence

ORD record
ord-335822cfcb2b437badd63309cfe36fb9
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

Loading…