Sodium hydride → 8-(2-Benzothiazolylthio)-5,6,7,8-tetrahydroquinoline

HRID 579974Notes

Reaction equation

HRID 579974 reaction equation
[H-].[Na+].[SH:3][C:4]1[S:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1.Cl[CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1>O1CCCC1>[S:5]1[C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=[C:4]1[S:3][CH:14]1[C:23]2[N:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH2:17][CH2:16][CH2:15]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 137121808-Chloro-5,6,7,8-tetrahydroquinolineHCID 178418395HCID 178418395, compound

Product 1

HCID 137121828-(2-Benzothiazolylthio)-5,6,7,8-tetrahydroquinolineYield 61.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.0 g (66.67 mmol) of 80% sodium hydride in oil were added to 9.97 g (59.1 mmol) of 2-mercaptobenzothiazole in 250 ml of dry tetrahydrofuran under nitrogen. The suspension was stirred at ambient temperature and, when effervescence had ceased 10 g (59.65 mmol) of 8-chloro-5,6,7,8-tetrahydroquinoline were added via a syringe. The reaction mixture was stirred at ambient temperature for 48 hours and the solvent was removed under reduced pressure. The residue was partitioned between water and dichloromethane and the organic phase was washed with water, dried over MgSO4 and concentrated to dryness under reduced pressure. The resulting oil was purified by flash column chromatography over silica (75 g)with elution with a mixture of dichloromethane and diethyl ether (1:0 gradually changing to 0:1). The pale yellow oil residue was crystallized from a mixture of dichloromethane-40°-60° petroleum ether to obtain 10.9 g (61%) of 8-(2-benzothiazolylthio)-5,6,7,8-tetrahydroquinoline in form of white crystals melting at 72° -3° C.

Workup

  1. additionwere added via a syringe
  2. stirringThe reaction mixture was stirred at ambient temperature for 48 hours
  3. customthe solvent was removed under reduced pressure
  4. customThe residue was partitioned between water and dichloromethane
  5. washthe organic phase was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated to dryness under reduced pressure
  8. customThe resulting oil was purified by flash column chromatography over silica (75 g)with elution with a mixture of dichloromethane and diethyl ether (1:0
  9. customThe pale yellow oil residue was crystallized from a mixture of dichloromethane-40°-60° petroleum ether

Sources & evidence

ORD record
ord-6f44966d1b9c425a90c2e4a08d344d95
Source dataset
uspto-grants-1988_06
Patent number
US04751233

Reaction notes

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