Hydrochloric Acid → HCID 178527725, compound

HRID 540344Notes

Reaction equation

HRID 540344 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]([N:12]2[CH2:18][CH2:17][CH2:16][C:15]3[CH:19]=[CH:20][CH:21]=[CH:22][C:14]=3[CH2:13]2)[CH:3]=1.C[S-:24].[Na+].Cl>CN(C)C=O.O>[CH2:13]1[C:14]2[CH:22]=[CH:21][CH:20]=[CH:19][C:15]=2[CH2:16][CH2:17][CH2:18][N:12]1[C:4]1[CH:3]=[C:2]([SH:24])[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 71255109HCID 71255109, compound

Product 1

HCID 178527725HCID 178527725, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 2-(4-chloroquinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine (2 g, 6.47 mmol) and sodium thiomethoxide (2.4 g, 34 mmol) in dry N,N-dimethylformamide (20 mL) was heated with stirring overnight under reflux. The reaction mixture was cooled to 50° C. and the volatile components were evaporated under reduced pressure to give a residue which was dissolved in 30 mL of chilled water and carefully acidified with 20% hydrochloride aid to pH 4-5 under argon. The resultant solution was extracted with chilled dichloromethane (30 mL×3). The dichloromethane fractions were combined and washed with chilled brine (30 mL×2) and then concentrated under reduced pressure at room temperature to give the crude product. It was used in next step without further purification.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux
  3. customthe volatile components were evaporated under reduced pressure
  4. customto give a residue which
  5. extractionThe resultant solution was extracted with chilled dichloromethane (30 mL×3)
  6. washwashed with chilled brine (30 mL×2)
  7. concentrationconcentrated under reduced pressure at room temperature

Sources & evidence

ORD record
ord-13e6c18dc96842c194b7f82a0d51ec62
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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