P-Anisidine → HCID 12852329, compound

HRID 1164395Notes

Reaction equation

HRID 1164395 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.[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=1.[H-].[Na+]>C(Cl)(Cl)Cl>[CH3:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][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)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 24758Sodium hydrideHCID 12852324HCID 12852324, compound

Product 1

HCID 12852329HCID 12852329, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

3,4-Dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole in the amount of 1.12 g (3 m mole) was dissolved in 30 ml of chloroform. Then, 0.44 g of p-anisidine (3.6 m mole) and a catalytic amount of sodium hydride were added under ice-cooled stirring conditions. The temperature of the mixture was allowed to rise to room temperature, and then refluxed for 12 hours. The reaction mixture was cooled and washed with water. After drying the chloroform layer over anhydrous magnesium sulfate, chloroform was evaporated under reduced pressure. The residue was chromatographed on silica gel and eluted with chloroform to obtain 0.28 g (yield: 31%) of the intended product, m.p. 155°-157° C.; IR νmaxKBr cm-1 : 3360, 3100-2800, 1430; Anal. Calcd. for C18H19N3OS: C, 66.44; H, 5.88; N, 12.91; S, 9.85; Found: C, 66.91; H, 5.90; N, 12.88; S, 9.70.

Workup

  1. temperaturecooled
  2. customto rise to room temperature
  3. temperaturerefluxed for 12 hours
  4. temperatureThe reaction mixture was cooled
  5. washwashed with water
  6. dry with materialAfter drying the chloroform layer over anhydrous magnesium sulfate, chloroform
  7. customwas evaporated under reduced pressure
  8. customThe residue was chromatographed on silica gel
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-511791d480e04172952ccbe3f09057a6
Source dataset
uspto-grants-1983_01
Patent number
US04369309

Reaction notes

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