6-methoxy-1H-benzimidazole-2-sulfinyl chloride → 8-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline

HRID 1088817Notes

Reaction equation

HRID 1088817 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][C:10]=2[CH2:12][Li])[CH2:5][CH2:4][CH2:3]1.[CH3:14][O:15][C:16]1[CH:27]=[CH:26][C:19]2[N:20]=[C:21]([S:23](Cl)=[O:24])[NH:22][C:18]=2[CH:17]=1>C1C=CC=CC=1>[CH3:14][O:15][C:16]1[CH:27]=[CH:26][C:19]2[N:20]=[C:21]([S:23]([CH2:12][C:10]3[CH:9]=[CH:8][CH:7]=[C:6]4[C:11]=3[N:2]([CH3:1])[CH2:3][CH2:4][CH2:5]4)=[O:24])[NH:22][C:18]=2[CH:17]=1

Participants

4

Reactant 2

HCID 221617996-methoxy-1H-benzimidazole-2-sulfinyl chlorideHCID 178506848HCID 178506848, compound

Product 1

HCID 150533118-(5-Methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinolineYield 3.6%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

(1-Methyl-1,2,3,4-tetrahydroquinolin-8-yl)methyl lithium (18.3 g) was dissolved in benzene (150 ml). After adding (5-methoxy-2-benzimidazolyl)sulfinyl chloride (20.1 g) thereto, the mixture was refluxed for 2 hours. The resulting lithium chloride was filtered off, and the filtrate was concentrated under reduced pressure. The resulting residue was recrystallized from ethyl acetate to give 8-(5-methoxy-2-benzimidazolyl)sulfinylmethyl-1-methyl-1,2,3,4-tetrahydroquinoline (1.1 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. filtrationThe resulting lithium chloride was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe resulting residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-c9cad37bb5064d61952da1ebe3d31a1f
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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