2-Chlorobenzaldehyde → 2',5-Dichloro-2-methylaminobenzhydrol

HRID 648109Notes

Reaction equation

HRID 648109 reaction equation
B(Cl)(Cl)[Cl:2].Cl[CH2:6][C:7]1C=CC(N)=CC=1.[Cl:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH:17]=[O:18].C([N:27]([CH2:32]CCC)[CH2:28][CH2:29][CH2:30][CH3:31])CCC>C1C=CC=CC=1.CCOCC.O>[CH3:32][NH:27][C:28]1[CH:29]=[CH:30][C:31]([Cl:2])=[CH:7][C:6]=1[CH:17]([OH:18])[C:16]1[CH:19]=[CH:20][CH:21]=[CH:22][C:15]=1[Cl:14]

Participants

8

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 7622TributylamineHCID 25135Boron TrichlorideHCID 113209864-Chloromethylaniline

Product 1

HCID 124217352',5-Dichloro-2-methylaminobenzhydrolYield 87.6%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolvent

Procedure

To a solution of boron trichloride (100 mg) in dry benzene (5 ml), a solution of p-chloromethylaniline (100 mg) in dry benzene (2 ml) is added with cold water cooling (7°-10° C.), and the resultant mixture is refluxed for 2 hours. Then, a solution of o-chlorobenzaldehyde (99 mg) and tri-n-butylamine (131 mg) in dry benzene (2 ml) is added thereto with cold water cooling, and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with ice pieces and shaken with ether. The ethereal layer is washed with aqueous sodium carbonate and a saturated brine in that order, dried over potassium carbonate, and evaporated under reduced pressure. The residue is chromatographed on a column of silica gel, and the product is recrystallized from chloroform-petroleum ether to give 2-methylamino-5,2'-dichlorobenzhydrol (174 mg) as crystals melting at 106° to 108° C. The yield is 87.4%.

Workup

  1. additionThe reaction mixture is mixed with ice pieces
  2. washThe ethereal layer is washed with aqueous sodium carbonate
  3. dry with materiala saturated brine in that order, dried over potassium carbonate
  4. customevaporated under reduced pressure
  5. customThe residue is chromatographed on a column of silica gel
  6. customthe product is recrystallized from chloroform-petroleum ether

Sources & evidence

ORD record
ord-7071e4e62997483088c8b1d3f6a26f82
Source dataset
uspto-grants-1983_10
Patent number
US04410730

Reaction notes

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