Chloral → N'-(2-Fluorophenyl)-N-methyl-N-(1,2,2,2-tetrachloroethyl)urea

HRID 435889Notes

Reaction equation

HRID 435889 reaction equation
[CH3:1][NH:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:4].O=[CH:14][C:15]([Cl:18])([Cl:17])[Cl:16].S(Cl)([Cl:21])=O>C(OCC)C>[CH3:1][N:2]([CH:14]([Cl:21])[C:15]([Cl:18])([Cl:17])[Cl:16])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])=[O:4]

Participants

5

Reactant 3

HCID 6407ChloralHCID 24386Thionyl ChlorideHCID 676515N-(2-fluorophenyl)-N'-methylurea

Product 1

HCID 12906107N'-(2-Fluorophenyl)-N-methyl-N-(1,2,2,2-tetrachloroethyl)urea

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

N-methyl-N'-o-fluorophenyl urea (16.8 g, 0.1 mol) was combined with 22.5 g (0.15 mol) chloral and 18.0 g (0.15 mol) thionyl chloride. After several minutes an exothermicity was noted and the reaction mixture became a homogenous yellow oil. After 5 minutes more, a precipitate began to form. After 11/2 hours a 3:1 mixture of diethyl ether:petroleum ether was added and the product was collected on a filter and dried. The solid, which weighed 25 g, melted at 130°-141° C. and analyzed as follows: %Cl, calculated 35.7, found 37.3; %N, calculated 9.5, found 9.5.

Workup

  1. waitAfter several minutes an exothermicity was noted
  2. customto form
  3. customthe product was collected on
  4. filtrationa filter
  5. customdried

Sources & evidence

ORD record
ord-cd443bb6c49f402e95303db3581073dd
Source dataset
uspto-grants-1977_02
Patent number
US04007033

Reaction notes

Loading…