Methyl iodide → HCID 178460731, compound

HRID 1733379Notes

Reaction equation

HRID 1733379 reaction equation
[NH:1]=[C:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:6]=1[NH:15][C:16]([NH:18][C:19]([O:21][CH3:22])=[O:20])=[S:17])[CH2:3][CH3:4].[OH-].[Na+].[CH3:25]I>CC(C)=O.O>[NH:1]=[C:2]([C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:6]=1[NH:15][C:16](=[N:18][C:19]([O:21][CH3:22])=[O:20])[S:17][CH3:25])[CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 20301199HCID 20301199, compound

Product 1

HCID 178460731HCID 178460731, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent2×

Procedure

To a suspension of 1-iminopropyl-2-(3-carbomethoxythioureido)-4-propylthiobenzene (1 g.; 0.00295 mole) in acetone (30 ml.) and water (15 ml.) there is added 50.8% aqueous sodium hydroxide (0.23 g.; 0.00295 mole). The solution that forms is stirred at room temperature for one hour and to it there is added methyl iodide (0.42 g.; 0.00295 mole). The turbid solution formed is stirred at room temperature for 30 minutes and is poured into water (500 ml.). The suspension formed is stirred at room temperature for one hour and is vacuum filtered. The filter cake is dried to afford 1-iminopropyl-2-(3-carbomethoxy-S-methylisothioureido)-4-propylthiobenzene (0.85 g.; 81.5%), m.p. 85°-90° C. (dec.).

Workup

  1. customThe turbid solution formed
  2. stirringis stirred at room temperature for 30 minutes
  3. customThe suspension formed
  4. stirringis stirred at room temperature for one hour
  5. filtrationfiltered
  6. customThe filter cake is dried

Sources & evidence

ORD record
ord-95a0880c4a1b4d108ca8a0204852df5c
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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