Dimethylamine → HCID 70528882, compound

HRID 1105793Notes

Reaction equation

HRID 1105793 reaction equation
[CH3:1][NH:2][CH3:3].Br[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24]>O1CCCC1>[ClH:24].[CH3:1][N:2]([CH3:3])[CH2:5][CH2:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH:16]=[CH:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[Cl:24]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 54125127HCID 54125127, compound

Product 1

HCID 70528882HCID 70528882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a mixture of 50 ml of tetrahydrofuran and 50 ml of aqueous 50% dimethylamine solution 5 g of 2-(4-bromobutoxy)-2'-chlorostilbene was dissolved and the resulting solution was stirred for 20 hours at ambient temperature. After the reaction was complete, the solvent was distilled off at reduced pressure. An aqueous 2 N NaOH solution was added to the residue and the mixture was extracted with ether. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. To the extract an ethanolic 20% hydrogen chloride was added to give 2-(4-dimethylaminobutoxy)-2'-chlorostilbene hydrochloride as a precipitate, which was then collected by filtration and recrystallized from ethanol-ether. Yield 4.7 g (94%). The data of melting point and elemental analysis are reported in the line of No. 1 in Table 2. Various compounds were also prepared in a similar manner. The data for these compounds are shown in Table 2.

Workup

  1. dissolutionwas dissolved
  2. distillationthe solvent was distilled off at reduced pressure
  3. additionAn aqueous 2 N NaOH solution was added to the residue
  4. extractionthe mixture was extracted with ether
  5. washThe extract was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. extractionTo the extract an ethanolic 20% hydrogen chloride
  8. additionwas added

Sources & evidence

ORD record
ord-850188c2e52b42d5afde57e08c48d49e
Source dataset
uspto-grants-1982_01
Patent number
US04310534

Reaction notes

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