Water → HCID 15053190, compound

HRID 1088826Notes

Reaction equation

HRID 1088826 reaction equation
[CH2:1]([Li])CCC.[N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]=1[S:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]([CH2:27][CH3:28])[CH2:24][CH2:23][C:22]2=O.O>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[N:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7]=1[S:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[C:21]2[C:26]=1[N:25]([CH2:27][CH3:28])[CH2:24][CH2:23][C:22]2=[CH2:1]

Participants

6

Reactant 3

HCID 962WaterHCID 14685766HCID 14685766, compoundHCID 178418339Butyllithium

Product 1

HCID 15053190HCID 15053190, compound

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

To a suspension of methyl triphenylphosphonium bromide (2.65 g)in tetrahydrofuran (50 ml) was added dropwise n-butyllithium (2.2 ml) in a nitrogen flow with stirring at -40° C. After raising the temperature to -20° C., a solution of 8-(2-benzimidazolyl)thiomethyl-1-ethyl-4-oxo-1,2,3,4-tetrahydroquinoline (500 mg) in tetrahydrofuran (5 ml) was added dropwise. The temperature was raised gradually to room temperature, and the mixture was stirred for 3 hours. Water was added to the reaction mixture, and the mixture was extracted with dichloromethane and dried over anhydrous magnesium sulfate. The residue obtained by distilling off the solvent was purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (3:1)] and recrystallized from diethyl ether-dichloromethane to give 8-(2-benzimidazolyl)thiomethyl-1-ethyl-4-methylene-1,2,3,4-tetrahydroquinoline (390 mg).

Workup

  1. temperatureAfter raising the temperature to -20° C.
  2. temperatureThe temperature was raised gradually to room temperature
  3. stirringthe mixture was stirred for 3 hours
  4. extractionthe mixture was extracted with dichloromethane
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe residue obtained
  7. distillationby distilling off the solvent
  8. customwas purified by silica gel column chromatography [eluent:n-hexane-ethyl acetate (3:1)]
  9. customrecrystallized from diethyl ether-dichloromethane

Sources & evidence

ORD record
ord-6c39f4f876b7429fa8935f2b9244105a
Source dataset
uspto-grants-1990_10
Patent number
US04963566

Reaction notes

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