Water → HCID 20572885, compound

HRID 2375285Notes

Reaction equation

HRID 2375285 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][CH2:5][CH2:6]Cl.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([SH:16])=[CH:12][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C=O)C>[CH3:2][N:3]([CH2:4][CH2:5][CH2:6][S:16][C:13]1[CH:14]=[CH:15][C:10]([Br:9])=[CH:11][CH:12]=1)[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 660494-BromothiophenolHCID 943083-(Dimethylamino)propyl chloride hydrochloride

Product 1

HCID 20572885HCID 20572885, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

3-(Dimethylamino)propyl chloride hydrochloride (3.48 g, 22 mmol) was added in portions to a suspension of 4-bromothiophenol (3.78 g, 20 mmol) and potassium carbonate (5.52 g, 40 mmol) in DMF (40 ml) and the reaction mixture heated to 60° C. for 15 minutes. The mixture was allowed to cool to ambient temperature and poured into water (100 ml) and extracted with EtOAc (2×100 ml). The extracts were combined, washed with brine (3×100 ml), dried (Chemelut column 1010) and evaporated to give the title compound (5.25 g, 96%) as a pale yellow oil. NMR 1.76 (m, 2H), 2.20 (s, 6H), 2.35 (t, 2H), 2.93 (t, 2H), 7.18 (d, 2H), 7.38 (d, 2H); m/z 276.

Workup

  1. temperatureto cool to ambient temperature
  2. extractionextracted with EtOAc (2×100 ml)
  3. washwashed with brine (3×100 ml)
  4. customdried (Chemelut column 1010)
  5. customevaporated

Sources & evidence

ORD record
ord-dca7f4b88f0e4d8295290a5b352dc813
Source dataset
uspto-grants-2008_12
Patent number
US07465728B2

Reaction notes

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