Methyl iodide → HCID 178503941, compound

HRID 1578048Notes

Reaction equation

HRID 1578048 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]([NH:12][C:13](=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[S:11].[C:21](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10](=[N:12][C:13](=[O:20])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[S:11][CH3:21]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 702451N-(((2,6-Dichlorophenyl)amino)thioxomethyl)benzamide

Product 1

HCID 178503941HCID 178503941, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

19.5 g (0.06 M) of N-(2,6-dichlorophenyl)-N'-benzoyl thiourea, 5.5 g (0.04 M) of ground potassium carbonate, 5.1 ml (0.08 M) of methyliodide and 200 ml of acetone are boiled in a reflux for 4 hours under energetic shaking. The acetone is distilled off. 200 ml of water are added to the residue and it is then filtered. The sediment on the filter is washed to a neutral pH. After drying 20.2 g (99% of the theoretical yield) of N-(2,6-dichlorophenyl)-N'-benzoyl-S-methylisothiourea are obtained with melting point 127-129° C. This product being recrystallized from ethyl alcohol gives the corresponding isothiourea with a melting point of 128°-130° C. and 85% yield of the theoretical one.

Workup

  1. temperaturea reflux for 4 hours under energetic shaking
  2. distillationThe acetone is distilled off
  3. addition200 ml of water are added to the residue and it
  4. filtrationis then filtered
  5. washThe sediment on the filter is washed to a neutral pH
  6. customAfter drying 20.2 g (99% of the

Sources & evidence

ORD record
ord-ef15b820fb874719afa9d02dcf3f0d1c
Source dataset
uspto-grants-1981_09
Patent number
US04290971

Reaction notes

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