Thionyl Chloride → HCID 21269549, compound

HRID 1194338Notes

Reaction equation

HRID 1194338 reaction equation
[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]2[N:12]=[C:13]([S:15][CH2:16][CH2:17]O)[NH:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:23])=O>C1C=CC=CC=1.C(#N)C>[ClH:23].[CH2:1]([C:8]1[CH:20]=[CH:19][C:11]2[N:12]=[C:13]([S:15][CH2:16][CH2:17][Cl:23])[NH:14][C:10]=2[CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 21269545HCID 21269545, compound

Product 1

HCID 21269549HCID 21269549, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 6342AcetonitrileSolvent

Procedure

12.1 g (40 mmoles) of 5-benzyl-2-(2-hydroxyethylthio)-benzimidazole are reacted with 5.15 ml of thionyl chloride in a mixture of 100 ml of benzene and 10 ml of acetonitrile. After teh evolution of the gas is ceased, the reaction mixture is evaporated, 30 ml of ethyl alcohol are added to the residue and the solution is evaporated off again. The product thus obtained is purified by chromatography. It is dissolved in ethyl acetate, introduced onto the colomn and thereafter eluted with ethyl acetate then ethanol. The target compound appears in the third fraction, its weight is 8.26 g. M.p.: 140°-145° C.

Workup

  1. customthe reaction mixture is evaporated
  2. addition30 ml of ethyl alcohol are added to the residue
  3. customthe solution is evaporated off again
  4. customThe product thus obtained
  5. customis purified by chromatography
  6. dissolutionIt is dissolved in ethyl acetate
  7. additionintroduced onto the colomn
  8. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-3b9c4c323eeb4aab87f02d9c1667a0d8
Source dataset
uspto-grants-1989_03
Patent number
US04814329

Reaction notes

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