Azobisisobutyronitrile → HCID 13210726, compound

HRID 464951Notes

Reaction equation

HRID 464951 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 etheral 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 etheral hydrochloric acid to the extract
  8. customthe hydrochloride of the title compound crystallized out

Sources & evidence

ORD record
ord-c9a5d1c0d9744681bfcf0d84847417a2
Source dataset
uspto-grants-1985_10
Patent number
US04550106

Reaction notes

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