Ammonium thiocyanate → 1-Methyl-1-(1-isothiocyanato-2,2,2-trichloroethyl)-3-(3,4-dichlorophenyl)urea

HRID 1995475Notes

Reaction equation

HRID 1995475 reaction equation
[CH3:1][N:2]([CH:14](Cl)[C:15]([Cl:18])([Cl:17])[Cl:16])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:4].[S-:20][C:21]#[N:22].[NH4+]>C(COC)OC>[CH3:1][N:2]([CH:14]([N:22]=[C:21]=[S:20])[C:15]([Cl:18])([Cl:17])[Cl:16])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([Cl:12])=[C:8]([Cl:13])[CH:7]=1)=[O:4]

Participants

4

Reactant 2

HCID 15666Ammonium thiocyanateHCID 129060331-Methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl)urea

Product 1

HCID 129061091-Methyl-1-(1-isothiocyanato-2,2,2-trichloroethyl)-3-(3,4-dichlorophenyl)urea

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

1-methyl-1-(1,2,2,2-tetrachloroethyl)-3-(3,4-dichlorophenyl)urea (7.7 g, 0.02 mol) was dissolved in 200 ml dimethoxyethane, followed by addition of 1.5 g (0.02 mol) of ammonium thiocyanate. The mixture was stirred for 2 hours, filtered and stripped of solvent. Ether was added to the residue, which was again filtered to remove a small amount of solid. The remaining solvent was then removed, leaving a dark oil which solidified upon standing. This material had a melting point of 142°-146° C. The infrared spectrum of the material showed a broad absorption band at 4.9 micron (for the --N=C=S group). Elemental analysis showed: %Cl, calc., 43.6, found 36.7; %S, calc. 7.9, found 6.3.

Workup

  1. filtrationfiltered
  2. additionEther was added to the residue, which
  3. filtrationwas again filtered
  4. customto remove a small amount of solid
  5. customThe remaining solvent was then removed
  6. customleaving a dark oil which

Sources & evidence

ORD record
ord-8209c9b95bef4205b0cc5c0a32bd41c5
Source dataset
uspto-grants-1983_09
Patent number
US04405355

Reaction notes

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