Hydrochloric Acid → HCID 22007460, compound

HRID 2268233Notes

Reaction equation

HRID 2268233 reaction equation
Cl.Cl.Cl.[NH2:4][CH2:5][CH2:6][C:7]1[N:8]=[CH:9][N:10]([CH2:12][CH2:13][CH2:14][NH:15][C:16]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)([CH3:18])[CH3:17])[CH:11]=1.[C:26]1([S:32](Cl)(=[O:34])=[O:33])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.Cl.[OH-].[Na+]>ClCCl.C(N(CC)CC)C>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]([C:16]([NH:15][CH2:14][CH2:13][CH2:12][N:10]2[CH:11]=[C:7]([CH2:6][CH2:5][NH:4][S:32]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)(=[O:34])=[O:33])[N:8]=[CH:9]2)([CH3:18])[CH3:17])=[CH:20][CH:21]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 18349657HCID 18349657, compound

Product 1

HCID 22007460HCID 22007460, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

Triethylamine (0.46 g) was added to a stirred suspension of 3-[4-(2-aminoethyl)imidazol-1-yl]-N-[1-(4-chlorophenyl)-1-methylethyl]propylamine trihydrochloride (0.65 g) in dichloromethane (20 ml). The solution was cooled to 0° C. and benzenesulphonyl chloride (0.27 g) in dichloromethane (10 ml) was added dropwise with stirring. The mixture was stirred at 0° C. for 30 minutes and then at ambient temperature for 3 hours. The mixture was washed with water, sodium bicarbonate solution and then dried, filtered and evaporated to give a yellow oil which was dissolved in alcohol and treated with ethereal hydrogen chloride. The resulting salt was hygroscopic and so was converted back to the free base by treatment with aqueous sodium hydroxide solution to give N-[2-(1-{3-[1-(4-chlorophenyl)-1-methylethylamino]-propyl}imidazol-4-yl)ethyl]benzenesulphonamide as an oil.

Workup

  1. stirringThe mixture was stirred at 0° C. for 30 minutes
  2. washThe mixture was washed with water, sodium bicarbonate solution
  3. customdried
  4. filtrationfiltered
  5. customevaporated
  6. customto give a yellow oil which

Sources & evidence

ORD record
ord-349afc3f540d4fd0940f93b0feeba799
Source dataset
uspto-grants-2001_12
Patent number
US06326500B1

Reaction notes

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