Methyl iodide → HCID 14031830, compound

HRID 986394Notes

Reaction equation

HRID 986394 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][CH2:13][CH:14]([CH3:16])[CH3:15])=[S:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1.[CH3:17][I:18]>CC(C)=O>[IH:18].[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([S:11][CH3:17])=[N:12][CH2:13][CH:14]([CH3:16])[CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 6328Methyl iodideHCID 8417409HCID 8417409, compound

Product 1

HCID 14031830HCID 14031830, compoundYield 55.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 53 g of N-[3,5-dichlorophenyl]-N'-[2-methylpropyl]thiourea in 200 ml of acetone was heated under reflux. A total of 16 ml of methyl iodide was added dropwise, heating is continued for a further 3 hours after this addition. The reaction mixture was then cooled and the precipitate collected to give 50 g (55.5%) of N-[3,5-dichlorophenyl]-N'-[2-methylpropyl]-carbamimidothioic acid, methyl ester, hydroiodide, m.p. 150° C. Concentration of the mother liquors and recrystallization in ethanol/isopropyl ether afforded a further 20 g of the product. Total yield: 77%.

Workup

  1. temperatureunder reflux
  2. temperatureheating
  3. additionafter this addition
  4. temperatureThe reaction mixture was then cooled
  5. customthe precipitate collected

Sources & evidence

ORD record
ord-dc2c1b0e197c49d78ba91c4eccd8fa28
Source dataset
uspto-grants-1987_12
Patent number
US04713382

Reaction notes

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