Formaldehyde → HCID 18980502, compound

HRID 2392737Notes

Reaction equation

HRID 2392737 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:15]=[CH:16][CH:17]=1)[CH2:6][O:7][CH:8]1[CH2:13][CH2:12][C:11](=[O:14])[CH2:10][CH2:9]1.[CH2:18]=O.Cl.[CH3:21][NH:22][CH3:23]>C(O)(=O)C>[CH3:21][N:22]([CH2:18][CH:10]1[CH2:9][CH:8]([O:7][CH2:6][C:5]2[CH:15]=[CH:16][CH:17]=[C:3]([O:2][CH3:1])[CH:4]=2)[CH2:13][CH2:12][C:11]1=[O:14])[CH3:23]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 10473Dimethylamine, hydrochlorideHCID 15816724HCID 15816724, compound

Product 1

HCID 18980502HCID 18980502, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
105 °C

Procedure

11.8 g (50 mmole) of compound (8), 0.84 g (28 mmole) paraformaldehyde and 2.26 g (28 mmole) dimethylamine hydrochloride were dissolved in 20 ml acetic acid and stirred for 15 minutes in a bath at 105° C. After evaporating off the solvent, the mixture was adjusted to an alkaline pH with aqueous sodium hydroxide solution and the Mannich base was extracted with dichloromethane. The solution was dried and the solvent was distilled off. 12.1 g (80% theoretical) of compound (9) were obtained.

Workup

  1. customAfter evaporating off the solvent
  2. extractionthe Mannich base was extracted with dichloromethane
  3. customThe solution was dried
  4. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-a210672788a141168a5a724c9ac9af60
Source dataset
uspto-grants-1998_09
Patent number
US05801201

Reaction notes

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