Chloral → 1-Methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl)urea

HRID 596728Notes

Reaction equation

HRID 596728 reaction equation
[Cl:1]C1C=C(NC(NC)=O)C=CC=1Cl.O=CC(Cl)(Cl)Cl.[Cl:20][C:21]1[CH:22]=[C:23]([NH:28][C:29]([N:31]([CH:33](O)[C:34]([Cl:37])([Cl:36])[Cl:35])[CH3:32])=[O:30])[CH:24]=[CH:25][C:26]=1[Cl:27].S(Cl)(Cl)=O>S(=O)(=O)(O)O.C(OCC)C>[CH3:32][N:31]([CH:33]([Cl:1])[C:34]([Cl:37])([Cl:36])[Cl:35])[C:29]([NH:28][C:23]1[CH:24]=[CH:25][C:26]([Cl:27])=[C:21]([Cl:20])[CH:22]=1)=[O:30]

Participants

7

Reactant 4

HCID 6407ChloralHCID 19113MonomethyldiuronHCID 24386Thionyl ChlorideHCID 129060321-(3,4-Dichlorophenyl)-3-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea

Product 1

HCID 129060331-Methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl)urea

Reagents, catalysts & solvents 2

HCID 1118Sulfuric AcidCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
65 °C

Procedure

1-(3,4-dichlorophenyl)-3-methyl urea (15.2 g, 0.07 mol) was combined with 15.0 g (0.1 mol) of chloral and 5 drops of concentrated sulfuric acid. The mixture was heated for an hour to effect reaction, then stripped under vacuum. To the crude 1-(3,4-dichlorophenyl)-3-(1-hydroxy-2,2,2-trichloroethyl)-3-methyl urea was added an excess of thionyl chloride and the mixture was heated gradually to a maximum of 65° C. Diethyl ether was added to the crude product, and the insoluble product was collected on a filter, washed twice with diethyl ether and dried. The 15.3 g of product, which melted at 132°-140° C., analyzed as follows: %Cl, calculated 55.2, found 46.0. The product is the seventh compound tabulated in Table I.

Workup

  1. temperatureThe mixture was heated for an hour
  2. customreaction
  3. customthe insoluble product was collected on a filter
  4. washwashed twice with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-e42fdc7c7b9a41faba903821c01656e6
Source dataset
uspto-grants-1977_03
Patent number
US04012225

Reaction notes

Loading…