Diethyl Ether → HCID 57159029, compound

HRID 1413054Notes

Reaction equation

HRID 1413054 reaction equation
[C:1]1([N:7]2[C:11](=[N:12][CH:13](Cl)[C:14]([Cl:17])([Cl:16])[Cl:15])[C:10](=[O:19])[N:9]([CH3:20])[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(CC)CC)C.C(OCC)C>C(#N)C>[C:1]1([N:7]2[C:11](=[N:12][CH:13]([NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:14]([Cl:17])([Cl:16])[Cl:15])[C:10](=[O:19])[N:9]([CH3:20])[C:8]2=[O:21])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 6115AnilineHCID 8471TriethylamineHCID 56977450HCID 56977450, compound

Product 1

HCID 57159029HCID 57159029, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In this Example 1-phenyl-3-methyl-5-(1,2,2,2-tetrachloroethyl)imino-1,3-diazolidine-2,4-dione (0.02 mol) was dissolved in 20 ml of acetonitrile and 0.02 mol of aniline then added. A mild exothermic reaction was observed. After ten minutes, triethylamine was added causing a very exothetmic reaction, which subsided within an hour to occur. The mixture was stirred for five hours and then 20 ml of ethyl ether added to assist precipitation of salts. The mixture was filtered and the filtrate evaporated off under high vacuum affording 1-phenyl-3-methyl-5-(1-phenylamino-2,2,2-trichloroethyl)imino-1,3-diazolidine-2,4-dione oil (Anal. calcd. for C18H15Cl3N4O2 --C50.79, H3.55, Cl24.98, N13.16 found C51.6, H3.8, Cl26.54, N12.2.

Workup

  1. customA mild exothermic reaction
  2. waitAfter ten minutes
  3. customa very exothetmic reaction, which
  4. waitsubsided within an hour
  5. customprecipitation of salts
  6. filtrationThe mixture was filtered
  7. customthe filtrate evaporated off under high vacuum

Sources & evidence

ORD record
ord-0feed986cc2f47d48ec09b47532cbc89
Source dataset
uspto-grants-1981_02
Patent number
US04248620

Reaction notes

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