Benzenesulfonyl chloride → HCID 18349662, compound

HRID 323957Notes

Reaction equation

HRID 323957 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-6ac2083ffbeb4b2f97de32423123ed8b
Source dataset
uspto-grants-2001_04
Patent number
US06215001B1

Reaction notes

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