tert-Butanol → HCID 20468213, compound

HRID 1903225Notes

Reaction equation

HRID 1903225 reaction equation
[ClH:1].[C:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]([S:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:6][CH:5]=1)#[N:3].C([OH:30])(C)(C)C.[OH-].[K+]>O>[ClH:1].[C:2]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[C:11]([S:20][CH2:21][CH2:22][N:23]([CH3:25])[CH3:24])=[N:12][C:13]3[C:18]([CH:19]=2)=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:8][CH:9]=1)(=[O:30])[NH2:3]

Participants

5

Reactant 3

HCID 6386tert-ButanolHCID 14797Potassium HydroxideHCID 13200256HCID 13200256, compound

Product 1

HCID 20468213HCID 20468213, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(p-cyanophenyl)-2-(2-dimethylaminoethylthio)quinoline hydrochloride (see Ex. 30, 0.65 g.), t-butanol (25 ml.) and potassium hydroxide (0.6 g.) was heated at 40° for 1 hr. Water (20 ml.) was added to the mixture and the t-butanol was evaporated. Additional water (20 ml.) was added, and the mixture was extracted with chloroform (3×30 ml.). The chloroform extract was washed with water (2×10 ml.) and dried (MgSO4). The solvent was evaporated and the residue was crystallised from ethanol. The crystalline material was dissolved in ethanol (50 ml.) and ethereal hydrogen chloride was added to the solution. The solvents were evaporated and the residue was crystallised from ethanol-diethyl ether to give 3-(p-carbamoylphenyl)-2-(2-dimethylaminoethylthio)quinoline hydrochloride, m.p. 253°-5°.

Workup

  1. temperaturewas heated at 40° for 1 hr
  2. customthe t-butanol was evaporated
  3. additionAdditional water (20 ml.) was added
  4. extractionthe mixture was extracted with chloroform (3×30 ml.)
  5. extractionThe chloroform extract
  6. washwas washed with water (2×10 ml.)
  7. dry with materialdried (MgSO4)
  8. customThe solvent was evaporated
  9. customthe residue was crystallised from ethanol
  10. dissolutionThe crystalline material was dissolved in ethanol (50 ml.)
  11. additionethereal hydrogen chloride was added to the solution
  12. customThe solvents were evaporated
  13. customthe residue was crystallised from ethanol-diethyl ether

Sources & evidence

ORD record
ord-e5474f6612c848eb926ce807ebb2cfc4
Source dataset
uspto-grants-1984_03
Patent number
US04435405

Reaction notes

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