p-Toluidine → HCID 178426631, compound

HRID 847399Notes

Reaction equation

HRID 847399 reaction equation
[CH2:1]([C:8]1[CH:16]=[CH:15][CH:14]=[CH:13][C:9]=1[C:10](O)=[Se:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH2:22])=[CH:20][CH:19]=1.C(N(CC)CC)C>ClCCl>[CH3:17][C:18]1[CH:24]=[CH:23][C:21]([NH:22][C:10](=[Se:11])[C:9]2[CH:13]=[CH:14][CH:15]=[CH:16][C:8]=2[CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 7813p-ToluidineHCID 8471TriethylamineHCID 178526205HCID 178526205, compound

Product 1

HCID 178426631HCID 178426631, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 4 g (0.013 mol) 2-benzylselenobenzoic acid in 80 ml dichloromethane is cooled to 0°-5° C. and treated with stirring with 2 g (0.015 mol) chloromethylenedimethyliminium chloride (Vilsmeir's reagent) in one portion. After 1 hour a solution of 1.47 g (0.0137 mol) 4-methylaniline and 3 g (0.03 mol) triethylamine are added dropwise in the cold and stirring continued for 2 hours at room temperature. The solution is washed successively with

Workup

  1. temperatureis cooled to 0°-5° C.
  2. additiontreated
  3. washThe solution is washed successively with

Sources & evidence

ORD record
ord-dcfd9f66b91d4b2998790426161a8da3
Source dataset
uspto-grants-1992_08
Patent number
US05141955

Reaction notes

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