Acetone → Dichloromaleic acid bis-furfurylamide

HRID 1277982Notes

Reaction equation

HRID 1277982 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-3667bdb3d8db41579f79b6752e3f59b2
Source dataset
uspto-grants-1981_07
Patent number
US04279921

Reaction notes

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