Acetone → Dichloromaleic acid bis-furfurylamide

HRID 1389805Notes

Reaction equation

HRID 1389805 reaction equation
[Cl:1]/[C:2](/[C:8](Cl)=[O:9])=[C:3](\[Cl:7])/[C:4](Cl)=[O:5].C(N([CH2:16][CH3:17])CC)C.[CH2:18]([NH2:24])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1.[OH2:25].[CH3:26][C:27]([CH3:29])=[O:28]>>[CH2:18]([N:24]([CH2:26][C:27]1[O:28][CH:17]=[CH:16][CH:29]=1)[C:4](=[O:5])/[C:3](/[Cl:7])=[C:2](/[Cl:1])\[C:8]([OH:9])=[O:25])[C:19]1[O:23][CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 5

HCID 180AcetoneHCID 962WaterHCID 3438FurfurylamineHCID 8471TriethylamineHCID 14792716Dichloromaleic acid dichloride

Product 1

HCID 86737444Dichloromaleic acid bis-furfurylamideYield 85%

Procedure

22.2 g (0.1 mol) of dichloromaleic acid dichloride were introduced slowly into a mixture of 20.2 g (0.2 mol) of triethylamine and 19.4 g (0.2 mol) of furfurylamine in 200 ml of acetone at room temperature, while stirring vigorously. The reaction mixture was poured into 100 ml of water and the product which precipitated was filtered off and dried. 29.0 g of dichloromaleic acid bis-furfurylamide of melting point 149° C. were obtained. The yield was 85% of theory.

Workup

  1. customthe product which precipitated
  2. filtrationwas filtered off
  3. customdried

Sources & evidence

ORD record
ord-745e3351612f486f9e79ed2db80380e1
Source dataset
uspto-grants-1981_01
Patent number
US04246279

Reaction notes

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