Benzaldehyde → HCID 12421740, compound

HRID 648114Notes

Reaction equation

HRID 648114 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:13]=[CH:12][C:9]([NH:10][CH3:11])=[CH:8][CH:7]=1)=[O:5])[CH3:2].B(Cl)(Cl)Cl.[CH:18](=[O:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N(CC)CC)C>C1C=CC=CC=1.CCOCC.O>[CH3:11][NH:10][C:9]1[CH:12]=[CH:13][C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[CH:7][C:8]=1[CH:18]([OH:25])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 4

HCID 240BenzaldehydeHCID 8471TriethylamineHCID 25135Boron TrichlorideHCID 319832ethyl 4-(methylamino)benzoate

Product 1

HCID 12421740HCID 12421740, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 241BenzeneSolvent3×HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of p-ethoxycarbonyl-methylaniline (179 mg) in dry benzene (2 ml), a solution of boron trichloride (129 mg) in dry benzene (2 ml), is added with ice cooling. A solution of benzaldehyde (0.1 ml) and triethylamine (222 mg) in dry benzene (3 ml) is added to the mixture, which is stirred at room temperature for 3 hours. The reaction mixture is mixed with water and shaken with ether. The organic layer is washed with water, dried, and evaporated to remove the solvents. The residue is washed with petroleum ether to give 2-methylamino-5-ethoxycarbonylbenzhydrol (196 mg) as crystals melting at 132° to 135° C. The yield is 69%.

Workup

  1. washThe organic layer is washed with water
  2. customdried
  3. customevaporated
  4. customto remove the solvents
  5. washThe residue is washed with petroleum ether

Sources & evidence

ORD record
ord-d2a1e5e739e24b089ea7ed5ee42a26b4
Source dataset
uspto-grants-1983_10
Patent number
US04410730

Reaction notes

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