Acetic Acid → HCID 13609084, compound

HRID 1589244Notes

Reaction equation

HRID 1589244 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][CH:8]=[C:7]([CH:11]([CH3:13])[CH3:12])[C:5]=1[NH2:6])([CH3:3])[CH3:2].C=O.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1.[C:22](O)(=O)C.Cl>C(O)C>[CH:11]([C:7]1[CH:8]=[C:9]([CH2:22][N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:10]=[C:4]([CH:1]([CH3:3])[CH3:2])[C:5]=1[NH2:6])([CH3:13])[CH3:12]

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 8083MorpholineHCID 32484Diisopropylaniline

Product 1

HCID 13609084HCID 13609084, compoundYield 172.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

A solution of 2,6-diisopropylaniline (35.45 g, 0.20 mol), 37% aqueous formaldehyde (16.2 mL, 0.20 mol), morpholine (17.42 g, 0.20 mol), acetic acid (6.00 g, 0.10 mol), and ethanol (25 mL) were reacted under conditions similar to Example 1. After concentration on the rotary evaporator, the residue was dissolved in diethyl ether and washed with aqueous sodium bicarbonate and water. After drying the ether solution, a solution of hydrogen chloride (0.20 mol) in ethanol was added. Filtration and drying gave the hydrochloride salt of the title compound (47.58 g, 76.0%). The salt (20.0 g, 0.6 mol) was dissolved in acetone and treated with solid potassium bicarbonate. Upon filtration and evaporation of solvent, the title compound was obtained (16.27 g, 92.2%).

Workup

  1. concentrationAfter concentration
  2. customon the rotary evaporator
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washwashed with aqueous sodium bicarbonate and water
  5. dry with materialAfter drying the ether solution
  6. filtrationFiltration
  7. customdrying

Sources & evidence

ORD record
ord-e80d9f657ee94020b6f0f760d8f29650
Source dataset
uspto-grants-1986_02
Patent number
US04568744

Reaction notes

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