3-(Diethylamino)-1-propanol → Bis(3-diethylaminopropyl)dibenzothiophene-2,8-dicarboxylate dihydrochloride

HRID 1578635Notes

Reaction equation

HRID 1578635 reaction equation
[CH:1]1[C:9]2[C:8]3[CH:10]=[C:11]([C:14]([Cl:16])=[O:15])[CH:12]=[CH:13][C:7]=3[S:6][C:5]=2[CH:4]=[CH:3][C:2]=1[C:17](Cl)=[O:18].[CH2:20]([N:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][OH:26])[CH3:21]>>[ClH:16].[ClH:16].[CH2:20]([N:22]([CH2:27][CH3:28])[CH2:23][CH2:24][CH2:25][O:26][C:17]([C:2]1[CH:3]=[CH:4][C:5]2[S:6][C:7]3[CH:13]=[CH:12][C:11]([C:14]([O:26][CH2:25][CH2:24][CH2:23][N:22]([CH2:27][CH3:28])[CH2:20][CH3:21])=[O:15])=[CH:10][C:8]=3[C:9]=2[CH:1]=1)=[O:18])[CH3:21]

Participants

3

Reactant 2

HCID 121593-(Diethylamino)-1-propanolHCID 12331810Dibenzothiophene-2,8-dicarbonyl chloride

Product 1

HCID 12331761Bis(3-diethylaminopropyl)dibenzothiophene-2,8-dicarboxylate dihydrochloride

Procedure

A solution of 7.6 g (0.025 mole) of dibenzothiophene-2,8 -dicarbonyl chloride and 6.5 g (0.05 mole) of 3-diethylaminopropanol in 1 liter of chlorofrom is heated at reflux for two hours. The solution is concentrated to 500 ml, diluted with petroleum ether (75°-90°) and the precipitated solid is crystallized from methanol-isopropanol and finally from water-acetone to yield bis(3-diethylaminopropyl)dibenzothiophene-2,8-dicarboxylate dihydrochloride, M.P. 243°-245°C.

Workup

  1. temperatureat reflux for two hours
  2. concentrationThe solution is concentrated to 500 ml
  3. additiondiluted with petroleum ether (75°-90°)
  4. customthe precipitated solid is crystallized from methanol-isopropanol and finally from water-acetone

Sources & evidence

ORD record
ord-7b5bab23ab1f4efda2b4260b650c5dcb
Source dataset
uspto-grants-1976_02
Patent number
US03937835

Reaction notes

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