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

HRID 596727Notes

Reaction equation

HRID 596727 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 product 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. The product is the sixth compound tabulated in Table I.

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-dac99c30401741b39d3cbf736e4bcb2c
Source dataset
uspto-grants-1977_03
Patent number
US04012225

Reaction notes

Loading…