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

HRID 435890Notes

Reaction equation

HRID 435890 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.

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-976af462241c44f2b6f242c9335103a7
Source dataset
uspto-grants-1977_02
Patent number
US04007033

Reaction notes

Loading…