Benzenesulfonyl chloride → HCID 18349662, compound

HRID 378617Notes

Reaction equation

HRID 378617 reaction equation
[C:1]1([S:7](Cl)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[N:11]1([CH2:16][CH2:17][CH2:18][NH:19][C:20]([C:23]2[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=2)([CH3:22])[CH3:21])[CH:15]=[CH:14][N:13]=[CH:12]1.C(N(CC)CC)C>ClCCl>[C:1]1([S:7]([O:29][C:26]2[CH:27]=[CH:28][C:23]([C:20]([NH:19][CH2:18][CH2:17][CH2:16][N:11]3[CH:15]=[CH:14][N:13]=[CH:12]3)([CH3:22])[CH3:21])=[CH:24][CH:25]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 8471TriethylamineHCID 18349573HCID 18349573, compound

Product 1

HCID 18349662HCID 18349662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A solution of benzenesulphonyl chloride (0.51 g) in dichloromethane (5 ml) was added in portions over 5 minutes to a solution of 4-{1-[3-(imidazol-1-yl)propylamino]-1-methylethyl}phenol (0.75 g) and triethylamine (0.29 g) in dichloromethane (5 ml) at 0° C. with stirring. The mixture was stirred at ambient temperature for 3 hours then diluted with dichloromethane and washed with water. The organic layer was separated, dried and evaporated. The residue was purified by flash column chromatography on silica using methanol as the mobile phase to give 4-{1-[3-(imidazol-1-yl)propylamino]-1-methylethyl}phenyl benzenesulphonate as an oil.

Workup

  1. stirringThe mixture was stirred at ambient temperature for 3 hours
  2. washwashed with water
  3. customThe organic layer was separated
  4. customdried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography on silica

Sources & evidence

ORD record
ord-6bc654afa1634eb698e52ab44fd34c21
Source dataset
uspto-grants-2000_02
Patent number
US06031109

Reaction notes

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