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

HRID 1080930Notes

Reaction equation

HRID 1080930 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, 0.0 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.

Workup

  1. temperaturecooled
  2. temperaturecooled to ice bath temperature

Sources & evidence

ORD record
ord-795706f61fc84cf0b735d40fa56584fa
Source dataset
uspto-grants-1996_12
Patent number
US05583261

Reaction notes

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