Water → HCID 12852327, compound

HRID 544359Notes

Reaction equation

HRID 544359 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]([NH2:30])[CH2:27][CH2:28][CH3:29].[H-].[Na+].O>C(Cl)(Cl)Cl>[CH2:26]([NH:30][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)[CH2:27][CH2:28][CH3:29]

Participants

6

Reactant 4

HCID 962WaterHCID 8007ButylamineHCID 24758Sodium hydrideHCID 12852324HCID 12852324, compound

Product 1

HCID 12852327HCID 12852327, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2.24 g of 3,4-dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole in chloroform (30 ml) was added 4 ml of n-butylamine. A catalytic amount of sodium hydride was thereafter added under ice-cooling, stirring conditions. After stirring for 15 minutes at room temperature, the mixturewas refluxed for 24 hours. The reaction mixture was cooled and then condensed under reduced pressure. The residue was added with water and extracted with chloroform. The extract was washed with water, dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 0.71 g (yield: 43.3%) of the intended product, m.p. 122°-124° C.; IR νmaxKBr cm-1 : 3320, 3100-2700, 1430; Anal. Calcd. for C15H21N3S: C, 65.42; N, 7.68; N, 15.26; S, 11.64; Found: C, 65.63; H, 7.61; N, 15.46; S, 11.30.

Workup

  1. temperaturecooling
  2. stirringAfter stirring for 15 minutes at room temperature
  3. temperaturethe mixturewas refluxed for 24 hours
  4. temperatureThe reaction mixture was cooled
  5. customcondensed under reduced pressure
  6. extractionextracted with chloroform
  7. washThe extract was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customChloroform was evaporated under reduced pressure
  10. customThe residue was chromatographed on silica gel
  11. washeluted with chloroform

Sources & evidence

ORD record
ord-9aa77c3d1a5c49379fdfc93f65aff247
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

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