Water → HCID 54555190, compound

HRID 1646994Notes

Reaction equation

HRID 1646994 reaction equation
[CH2:1]([C:5]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22]Br)=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:8]2[CH:24]=[CH:25][CH:26]=[CH:27][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4].[CH2:28]([NH2:32])[CH2:29][CH2:30][CH3:31].O>CS(C)=O>[CH2:1]([C:5]1[N:9]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21][CH2:22][N:32]([CH2:5][CH2:1][CH2:2][CH3:3])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[C:8]2[CH:24]=[CH:25][CH:26]=[CH:27][C:7]=2[N:6]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 8007ButylamineHCID 53856773HCID 53856773, compound

Product 1

HCID 54555190HCID 54555190, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 0.0017 mol of 2-n-butyl-1-(4-bromopropoxy-benzenesulphonyl) benzimidazole in 15 ml of dimethylsulphoxide was added 0.0034 mol of n-butylamine. The reaction medium was allowed to stand for 17 hours at room-temperature and then poured into 50 ml of water. After extraction, the ethereal phase was dried and evaporated to dryness. The residue so obtained was purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate) to obtain an oil which was the desired product in the form of the free base (yield: 50%). The oxalate of the base so provided was formed by dissolving the base in question into ethyl ether and adding an ethereal solution of oxalic acid.

Workup

  1. extractionAfter extraction
  2. customthe ethereal phase was dried
  3. customevaporated to dryness
  4. customThe residue so obtained
  5. customwas purified by chromatography on a silica column (eluent: dichloromethane/ethyl acetate)
  6. customto obtain an oil which

Sources & evidence

ORD record
ord-36735c766ecf46b5860ec04f5b804997
Source dataset
uspto-grants-1993_01
Patent number
US05182291

Reaction notes

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