Diethylamine → HCID 12852330, compound

HRID 544362Notes

Reaction equation

HRID 544362 reaction equation
O1CCCC1.C1(C)C=CC(S(O[CH2:16][CH:17]2[S:29][C:21]3=[N:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=4[N:20]3[CH2:19][CH2:18]2)(=O)=O)=CC=1.[CH2:31]([NH:33][CH2:34][CH3:35])[CH3:32].[H-].[Na+]>O>[CH2:31]([N:33]([CH2:16][CH:17]1[S:29][C:21]2=[N:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[N:20]2[CH2:19][CH2:18]1)[CH2:34][CH3:35])[CH3:32]

Participants

6

Reactant 4

HCID 8021DiethylamineHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 12852324HCID 12852324, compound

Product 1

HCID 12852330HCID 12852330, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into 20 ml of tetrahydrofuran was dissolved 1.12 g (3 m mole) of 3,4-dihydro-2-p-toluenesulfonyloxymethyl-2H-(1,3)-thiazino[3,2-a]benzimidazole, followed by the addition of 5 ml of diethylamine. Then, a catalytic amount of sodium hydride was added under ice-cooled stirring conditions. The temperature of the mixture was allowed to rise to room temperature andthen refluxed for eight hours. The reaction mixture was cooled and then condensed under reduced pressure. The reaction product was added with water and then extracted with chloroform. The chloroform layer was then dried over anhydrous magnesium sulfate. Chloroform was evaporated under reduced pressure. The residue was chromatographed on silica gel and elutedwith chloroform to obtain 0.33 g (yield: 40%) of the intended product, m.p.93°-94° C.; IR νmaxKBr cm-1 : 3100-2800, 1420; Anal. Calcd. for C15H21N3S: C, 65.42; H, 7.68; N, 15.26; S, 11.64; Found: C, 65.33; H, 7.77; N, 15.49; S, 11.41.

Workup

  1. temperaturecooled
  2. customto rise to room temperature
  3. temperatureandthen refluxed for eight hours
  4. temperatureThe reaction mixture was cooled
  5. customcondensed under reduced pressure
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform layer was then dried over anhydrous magnesium sulfate
  8. customChloroform was evaporated under reduced pressure
  9. customThe residue was chromatographed on silica gel and elutedwith chloroform

Sources & evidence

ORD record
ord-88c2160d28384e86bf99b0c5813ce747
Source dataset
uspto-grants-1984_05
Patent number
US04450109

Reaction notes

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