4-Toluenesulfonyl chloride → HCID 13015892, compound

HRID 1414048Notes

Reaction equation

HRID 1414048 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]2[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=2[N:6]=[C:5]1[CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1>N1C=CC=CC=1>[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([O:1][CH2:2][CH2:3][N:4]2[C:8]3[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=3[N:6]=[C:5]2[CH2:14][CH2:15][NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:32])=[O:31])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 13015889HCID 13015889, compound

Product 1

HCID 13015892HCID 13015892, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 1.5 g. (4.6 mmole) of 1-(2-hydroxy ethyl)-2-(2-t-butoxycarbonylaminoethyl)-6-chlorobenzimidazole prepared in Step B. above and 1.0 g. (5.5 mmole) p-toluenesulfonyl chloride in 7.5 ml. of dry pyridine is heated at 50° C. for 2 hours. After cooling the reaction mixture is partitioned between dichloromethane and saturated sodium hydrogencarbonate solution. The organic extracts are dried with calcium sulfate and concentrated to remove solvent. The remaining pyridine is removed by azeotroping with toluene. The desired product, 1.6 g. (70%), is obtained as a crystalline solid.

Workup

  1. temperatureAfter cooling the reaction mixture
  2. customis partitioned between dichloromethane and saturated sodium hydrogencarbonate solution
  3. dry with materialThe organic extracts are dried with calcium sulfate
  4. concentrationconcentrated
  5. customto remove solvent
  6. customThe remaining pyridine is removed
  7. customby azeotroping with toluene
  8. custom(70%), is obtained as a crystalline solid

Sources & evidence

ORD record
ord-1f389aa5dc4445ab9beeaec26a2de568
Source dataset
uspto-grants-1981_02
Patent number
US04252816

Reaction notes

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