Azobisisobutyronitrile → HCID 13210726, compound

HRID 1979710Notes

Reaction equation

HRID 1979710 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][N:12]([CH3:14])[CH2:11][C:10]3[S:15][C:16]([CH3:18])=[CH:17][C:9]2=3)=[CH:4][CH:3]=1.BrN1[C:24](=[O:25])CCC1=O.N(C(C)(C)C#N)=NC(C)(C)C#N.C[O-].[Na+]>C(Cl)(Cl)(Cl)Cl.CO.O>[CH3:24][O:25][CH2:18][C:16]1[S:15][C:10]2[CH2:11][N:12]([CH3:14])[CH2:13][CH:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:9]=2[CH:17]=1

Participants

8

Reactant 4

HCID 6547AzobisisobutyronitrileHCID 67184N-bromobutanimideHCID 10942334Sodium MethoxideHCID 20261491HCID 20261491, compound

Product 1

HCID 13210726HCID 13210726, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 5943Carbon TetrachlorideSolvent

Procedure

2.79 gm (0.01 -ol) of 4-(p-chloro-phenyl)-2,6-dimethyl-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine were dissolved in 50 ml of carbon tetrachloride, the solution was heated at its boiling point with 1.8 gm of N-bromo-succinimide and 0.1 gm of azo-bis-isobutyronitrile for several hours. The resulting succinimide was suction-filtered off, and the solvent was removed in a rotary evaporator. The residue was admixed with a solution of 0.01 mol of sodium methoxide in methanol, and the mixture was heated at its boiling point for a short time. Then, water was added, and the resulting mixture was extracted with ether. Upon addition of ethereal hydrochloric acid to the extract, the hydrochloride of the title compound crystallized out.

Workup

  1. temperaturethe solution was heated at its
  2. customfor several hours
  3. filtrationThe resulting succinimide was suction-filtered off
  4. customthe solvent was removed in a rotary evaporator
  5. temperaturethe mixture was heated at its boiling point for a short time
  6. extractionthe resulting mixture was extracted with ether
  7. additionUpon addition of ethereal hydrochloric acid to the extract
  8. customthe hydrochloride of the title compound crystallized out

Sources & evidence

ORD record
ord-730dbc5220a0473da919837195ae7caa
Source dataset
uspto-grants-1984_11
Patent number
US04482559

Reaction notes

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