Water → HCID 12852328, compound

HRID 544360Notes

Reaction equation

HRID 544360 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]([NH2:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.[H-].[Na+].O>C(Cl)(Cl)Cl>[CH2:26]([NH:33][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)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 24758Sodium hydrideHCID 12852324HCID 12852324, compound

Product 1

HCID 12852328HCID 12852328, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1.12 g of 3,4-dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole in chloroform (20 ml) was added with 0.41 g of benzylamine and a catalytic amount of sodium hydride, and refluxed for 11 hours. The reaction mixture was cooled and then condensed under reduced pressure. Theresidue was added with water, extracted with chloroform. The extract was washed with water, 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 0.29 g (Yield: 31%) of theintended product, m.p. 155°-156° C.; IR νmaxKBr cm-1 : 3260, 3100-2800, 1600, 1420; Anal. Calcd. for C18H19N3S: C, 69.87; H, 6.19; N, 13.58; S, 10.36; Found: C, 70.00; H, 6.21; N, 13.69; S, 10.10.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customcondensed under reduced pressure
  3. extractionextracted with chloroform
  4. washThe extract was washed with water
  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-e0ad2d794c9a444b9fd63e9f6b02b6d5
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

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