Dipropylamine → HCID 12852331, compound

HRID 544363Notes

Reaction equation

HRID 544363 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.[CH2:26]([NH:29][CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28].O1CCOCC1>O>[CH2:26]([N:29]([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)[CH2:30][CH2:31][CH3:32])[CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8902DipropylamineHCID 312751,4-DioxaneHCID 12852324HCID 12852324, compound

Product 1

HCID 12852331HCID 12852331, compoundYield 14.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.12 g of 3,4-dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole were added 4 ml of di-n-propylamine and 20 ml of dioxane. The mixture was reacted in a sealed tube, at 120° C. and for 67 hours. After cooling down the temperature of the reaction mixture, it was condensed under reduced pressure. Water was added to the condensed reaction mixture,followed by an extraction with chloroform and dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure and the residue was chromatographed on silica gel and eluted with chloroform to obtain 0.13 g (yield: 14.3%) of the intended product, m.p. 82°-84° C.; IR νmaxKBr cm-1 : 3100-2700, 1420; Anal. Calcd. for C17H25N3S: C, 67.29; N, 8.30; N, 13.85; S, 10.56; Found: C, 67.52; H, 8.41; N, 13.98; S, 10.09.

Workup

  1. customThe mixture was reacted in a sealed tube, at 120° C. and for 67 hours
  2. temperatureAfter cooling down the temperature of the reaction mixture, it
  3. customcondensed under reduced pressure
  4. extractionmixture,followed by an extraction with chloroform
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customChloroform was evaporated under reduced pressure
  7. customthe residue was chromatographed on silica gel
  8. washeluted with chloroform

Sources & evidence

ORD record
ord-bad1b23e15bf471d8d9dd078d2d936fe
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

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