Chloral → HCID 70579302, compound

HRID 1413053Notes

Reaction equation

HRID 1413053 reaction equation
[CH3:1][N:2]1[C:6](=[NH:7])[C:5](=[O:8])[N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15].O=[CH:17][C:18]([Cl:21])([Cl:20])[Cl:19].S(Cl)([Cl:24])=O>COCCOC>[CH3:1][N:2]1[C:6](=[N:7][CH:17]([Cl:24])[C:18]([Cl:21])([Cl:20])[Cl:19])[C:5](=[O:8])[N:4]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:3]1=[O:15]

Participants

5

Reactant 3

HCID 6407ChloralHCID 24386Thionyl ChlorideHCID 20292815HCID 20292815, compound

Product 1

HCID 70579302HCID 70579302, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

In this preparation 1-methyl-3-phenyl-5-imino-1,3-diazolidine-2,4-dione (10.15 g; 0.05 mol) was dissolved in 80 ml 1,2-dimethoxyethane. Chloral (13.7 g, 1.0 mol) was added followed by the addition of thionyl chloride (11.9 g, 1.0 mol). The temperature of the reaction mixture rose to 45° C. due to the exothermicity of the reaction. One hour later the temperature was back to 23° C. and a solid had formed. The solid (1.1 g) had a melting point 140-150 with some not melting at all. The filtrate was stripped to give 9.6 g of a crude material which was recrystallized from benzene and washed with ether to give 8.2 g (0.02 mol) of 1-methyl-3-phenyl-5-(1,2,2,2-tetrachloroethyl)imino-1,3-diazolidine-2,4-dione melting at 158°-160° C.

Workup

  1. customThe temperature of the reaction mixture rose to 45° C. due to the exothermicity of the reaction
  2. customOne hour
  3. customwas back to 23° C.
  4. customa solid had formed
  5. customto give 9.6 g of a crude material which
  6. customwas recrystallized from benzene
  7. washwashed with ether

Sources & evidence

ORD record
ord-bd662816d9154032a6770bf97906be76
Source dataset
uspto-grants-1981_02
Patent number
US04248620

Reaction notes

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