Triethylamine → N-(2,6-Diisopropyl-phenyl)-malonamic acid ethyl ester

HRID 1013609Notes

Reaction equation

HRID 1013609 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(N(CC)CC)C.C([CH:23]([C:27](Cl)=[O:28])[C:24](Cl)=[O:25])C.[C:30](OCC)(=[O:32])[CH3:31]>>[CH2:30]([O:32][C:27](=[O:28])[CH2:23][C:24]([NH:6][C:5]1[C:4]([CH:1]([CH3:3])[CH3:2])=[CH:10][CH:9]=[CH:8][C:7]=1[CH:11]([CH3:13])[CH3:12])=[O:25])[CH3:31]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 32484DiisopropylanilineHCID 109209242-Ethylpropanedioyl dichloride

Product 1

HCID 44375808N-(2,6-Diisopropyl-phenyl)-malonamic acid ethyl ester

Conditions

Temperature
0 °C

Procedure

A 5 L 4-necked flask was fitted with a mechanical stirrer and temperature probe and then purged with nitrogen. The flask was charged with 200 mL (188 g, 1.06 mol) of 2,6-diisopropyl aniline, 163 mL (118 g, 1.17 mol) of triethylamine and 2.5 L of ethyl acetate. The clear, yellow solution was cooled to 0° C. with stirring and 143 mL (168 g, 95% pure, 1.06 mol) of ethyl malonyl chloride was added over 15 min. The internal temperature rose as high as 22° C. during the addition. The cold bath was removed and the yellow suspension was stirred for 100 min (HPLC indicated reaction completion). The suspension was filtered and the filtrate was evaporated at the Rotavap giving yellowish solids. The crude ester were then recrystallized from 3.0 L of heptane yielding 240.24 g (78%) of N-(2,6-Diisopropyl-phenyl)-malonamic acid ethyl ester as slightly yellow solids. HPLC analysis indicated >99% (a/a) purity. The materials 1H-NMR spectrum was consistent with structure

Workup

  1. customA 5 L 4-necked flask was fitted with a mechanical stirrer
  2. customtemperature probe and then purged with nitrogen
  3. additionThe internal temperature rose as high as 22° C. during the addition
  4. customThe cold bath was removed
  5. stirringthe yellow suspension was stirred for 100 min
  6. custom(HPLC indicated reaction completion)
  7. filtrationThe suspension was filtered
  8. customthe filtrate was evaporated at the Rotavap
  9. customgiving yellowish solids
  10. customThe crude ester were then recrystallized from 3.0 L of heptane yielding 240.24 g (78%) of N-(2,6-Diisopropyl-phenyl)-malonamic acid ethyl ester as slightly yellow solids

Sources & evidence

ORD record
ord-53bae29d6937479ea227881cff8b7a33
Source dataset
uspto-grants-2011_07
Patent number
US07981936B2

Reaction notes

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