Hexamethylenetetramine → N1-(5-formyl-2-methoxybenzyl)-2,4-dichlorobenzamide

HRID 1816590Notes

Reaction equation

HRID 1816590 reaction equation
C1N2CN3CN(C2)CN1C3.[CH3:11][O:12][C:13]1[CH:30]=[CH:29][CH:28]=[CH:27][C:14]=1[CH2:15][NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25].FC(F)(F)[C:33](O)=[O:34]>>[CH:33]([C:28]1[CH:29]=[CH:30][C:13]([O:12][CH3:11])=[C:14]([CH:27]=1)[CH2:15][NH:16][C:17](=[O:26])[C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[O:34]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6422Trifluoroacetic acidHCID 7960612,4-dichloro-N-[(2-methoxyphenyl)methyl]benzamide

Product 1

HCID 22493896N1-(5-formyl-2-methoxybenzyl)-2,4-dichlorobenzamide

Conditions

Temperature
50 °C

Procedure

9.04 g of hexamethylene tetramine was added to a solution of 10.0 g N1-(2-methoxybenzyl)-2,4-dichlorobenzamide in trifluoroacetic acid (200 mL), followed by stirring at 50° C. for 23 hours. The reaction solution was left and cooled to room temperature and then concentrated. The residue was diluted with ice-water and adjusted to pH 11 to 12 with 1N aqueous sodium hydroxide solution. The solution was extracted with ethyl acetate. The organic layer was washed with 1 N aqueous sodium hydroxide solution (×3), 1 N hydrochloric acid (×2) and brine, dried over anhydrous sodium sulfate and filtered thorough 100 g silica gel. After concentrating the filtrate, the residue was suspended in ethyl acetate. The solid was collected by filtration and washed with ethyl acetate, to give 7.15 g of N1-(5-formyl-2-methoxybenzyl)-2,4-dichlorobenzamide as a colorless solid.

Workup

  1. waitThe reaction solution was left
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. additionThe residue was diluted with ice-water
  5. extractionThe solution was extracted with ethyl acetate
  6. washThe organic layer was washed with 1 N aqueous sodium hydroxide solution (×3), 1 N hydrochloric acid (×2) and brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered thorough 100 g silica gel
  9. concentrationAfter concentrating the filtrate
  10. filtrationThe solid was collected by filtration
  11. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-ed3cda8810054e43b7282b19a46341ea
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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