Diethylamine → Trans-N,N,N',N'-tetraethyl-1,2-dimethylcyclohex-1-ene-4,5-dicarboxamide

HRID 128772Notes

Reaction equation

HRID 128772 reaction equation
[CH3:1][C:2]1[CH2:7][C@@H:6]([C:8]([OH:10])=O)[C@H:5]([C:11]([OH:13])=O)[CH2:4][C:3]=1[CH3:14].S(Cl)(Cl)=O.[CH2:19]([NH:21][CH2:22][CH3:23])[CH3:20]>C(OCC)C>[CH2:19]([N:21]([CH2:22][CH3:23])[C:8]([C@H:6]1[C@H:5]([C:11]([N:21]([CH2:22][CH3:23])[CH2:19][CH3:20])=[O:13])[CH2:4][C:3]([CH3:14])=[C:2]([CH3:1])[CH2:7]1)=[O:10])[CH3:20]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 738867trans-1,2-Dimethylcyclohexene-4,5-dicarboxylic acid

Product 1

HCID 67746645Trans-N,N,N',N'-tetraethyl-1,2-dimethylcyclohex-1-ene-4,5-dicarboxamide

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To trans-1,2-dimethylcyclohexene-4,5-dicarboxylic acid (1.98 g 0.01 mol) heated to 80° C., was added thionyl chloride (2.38 g, 0.02 mol) over 1 hr. The mixture was kept at this temperature for a further two hours, then cooled and added dropwise to a diethyl ether solution (45 ml) of excess diethylamine (14.6 g, 0.2 mol) cooled to ice bath temperature. The solvent was removed to give the crude product as an oil which was not purified for use in the next stage.

Workup

  1. temperaturecooled
  2. temperaturecooled to ice bath temperature
  3. customThe solvent was removed

Sources & evidence

ORD record
ord-8bddd387f21d4a6a8aebe4fbe66f786c
Source dataset
uspto-grants-1995_11
Patent number
US05464873

Reaction notes

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