Hexane → HCID 178469478, compound

HRID 1680527Notes

Reaction equation

HRID 1680527 reaction equation
C(O[C:4](=[O:20])[C:5](=[CH:11][NH:12][C:13]1[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[CH:14]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])C.CCCCCC>C1(OC2C=CC=CC=2)C=CC=CC=1>[CH2:9]([O:8][C:6]([C:5]1[CH:11]=[N:12][C:13]2[CH2:18][CH2:17][CH2:16][C:15](=[O:19])[C:14]=2[C:4]=1[OH:20])=[O:7])[CH3:10]

Participants

4

Reactant 2

HCID 8058HexaneHCID 12877078diethyl N-(3-oxo-1-cyclohexen-1-yl)-aminomethylenemalonate

Product 1

HCID 178469478HCID 178469478, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 7583Diphenyl EtherSolvent2×

Procedure

Diphenyl ether (20 ml) was heated to 260° C. or above, and a solution of 6.87 g of N-(3-oxo-1-cyclohexen-1-yl)aminomethylenemalonic acid diethyl ester in 5 ml of diphenyl ether was added thereto drop by drop. The resulting reaction mixture was refluxed for 15 minutes. After being allowed to cool, the reaction mixture was poured into 300 ml of n-hexane. The precipitate so formed was separated by filtration and then purified to obtain a yield of 4.37 g of the desired compound in the form of a pale-yellow powder. This compound melted (and decomposed) at 221°-224° C. Its infrared absorption spectrum (KBr tablet) had absorption peaks at 3340, 2960, 1740, 1690, 1635, 1605, 1560, 1510, 1285, 1170, 1150, 1090, 1035, 920 and 815 cm-1, and its n.m.r. spectrum (d6 -DMSO, 60Mc, TMS) had signals at δ values of 1.31 (3H, t, J=7 Hz), 1.9-3.1 (6H, m), 4.27 (2H, q, J=7 Hz), and 8.55 (1H, s).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 15 minutes
  3. temperatureto cool
  4. customThe precipitate so formed
  5. customwas separated by filtration
  6. custompurified

Sources & evidence

ORD record
ord-15388353c75f4f5fb470d1f4c6d561f7
Source dataset
uspto-grants-1981_06
Patent number
US04273932

Reaction notes

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