Thionyl Chloride → HCID 53703385, compound

HRID 355070Notes

Reaction equation

HRID 355070 reaction equation
S(Cl)(Cl)=O.[O:5]=[C:6]1[N:10]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]([OH:20])=[O:19])[C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[N:7]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>>[CH2:23]([O:19][C:18](=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][N:10]1[C:9]2[CH:21]=[CH:22][CH:23]=[CH:24][C:8]=2[N:7]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[C:6]1=[O:5])[CH2:24][CH2:8][CH2:9][CH2:21][CH3:22]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 12961179HCID 12961179, compound

Product 1

HCID 53703385HCID 53703385, compound

Procedure

5 cc. of thionylchloride are added to 1 g. of 8-(2-oxo-3-phenyl-benzimidazolin-1-yl)-caprylic acid and the mixture is stirred at room temperature for 2 hours. Unreacted thionylchloride is evaporated in a vacuum, the residue is dissolved in a small amount of anhydrous chloroform and 238 mg. of hexanol are added to the solution. The mixture is stirred at room temperature for 4 hours, consequetively washed with 5% NaHCO3 solution and water, dried over Na2SO4 and evaporated in a vacuum. The residue is further purified chromatographically on silicic acid gel using hexane/ethyl acetate as eluant.

Workup

  1. customUnreacted thionylchloride is evaporated in a vacuum
  2. dissolutionthe residue is dissolved in a small amount of anhydrous chloroform and 238 mg
  3. additionof hexanol are added to the solution
  4. washconsequetively washed with 5% NaHCO3 solution and water
  5. dry with materialdried over Na2SO4
  6. customevaporated in a vacuum
  7. customThe residue is further purified chromatographically on silicic acid gel

Sources & evidence

ORD record
ord-19bd902d0df044e49a6c1a689dbc4bdf
Source dataset
uspto-grants-1983_03
Patent number
US04377695

Reaction notes

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