1,4-Dioxane → HCID 12852326, compound

HRID 544358Notes

Reaction equation

HRID 544358 reaction equation
C1(C)C=CC(S(O[CH2:11][CH:12]2[S:24][C:16]3=[N:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=4[N:15]3[CH2:14][CH2:13]2)(=O)=O)=CC=1.O.[NH3:27].O1CCOCC1>O>[NH2:27][CH2:11][CH:12]1[S:24][C:16]2=[N:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[N:15]2[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 12852324HCID 12852324, compoundHCID 12896473Azane;hydrate

Product 1

HCID 12852326HCID 12852326, compoundYield 35.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To 2.24 g of 3,4-dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole, were added 5 g of 25% ammonia water and 40 ml of dioxane. The mixturewere heated in a sealed tube, at 120° C., for 75 hours. The reactionmixture was then 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 0.46 g (yield: 35.1%) of the intended product, m.p. 217°-222° C.; IR νmaxKBr cm-1 3300-2600, 1440; Anal. Calcd. for C11H13N3S: C, 60.25; H, 5.97; N, 19.16; S, 14.62; Found: C, 60.28; H, 5.99; N, 19.60; S, 14.13.

Workup

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

Sources & evidence

ORD record
ord-115ca27e32ea411ebed6e21aed13788b
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

Loading…