Methyl iodide → N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-dithiocarbamate methyl ester

HRID 2051583

Reaction equation

HRID 2051583 reaction equation
[C:1]1([NH:7][C:8]2[CH:13]=[CH:12][C:11]([NH:14][CH:15]([CH3:20])[CH2:16][CH:17]([CH3:19])[CH3:18])=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:21](=[S:23])=[S:22].[OH-].[Na+].[CH3:26]I>O1CCCC1>[CH3:26][S:22][C:21](=[S:23])[N:14]([C:11]1[CH:12]=[CH:13][C:8]([NH:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[CH:9][CH:10]=1)[CH:15]([CH3:20])[CH2:16][CH:17]([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 6348Carbon DisulfideHCID 131011,4-Benzenediamine, N-(1,3-dimethylbutyl)-N'-phenyl-HCID 14798Sodium Hydroxide

Product 1

HCID 19832493N-(4-anilinophenyl)-N-(1,3-dimethyl-butyl)-dithiocarbamate methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-phenyl-N'-(1,3-dimethylbutyl)-p-phenylenediamine (26.8g, 0.10 mol) is dissolved in 100 mL tetrahydrofuran in a 250 mL, 3-neck round bottom flask. Carbon disulfide (7.6g, 0.10 mol) is added over 0.5 hours with the concurrent addition of an aqueous solution of sodium hydroxide (4.0g, 0.10 mol). When addition is complete, methyl iodide (14.2g, 0.10 mol) is added and the mixture refluxed for 1 hour. The solvent is then stripped off on a rotary evaporator and the residue extracted with methylene chloride. The extract is dried with MgSO4 and the solvent is again removed on the rotary evaporator to yield the product.

Workup

  1. additionWhen addition
  2. temperaturethe mixture refluxed for 1 hour
  3. customThe solvent is then stripped off on a rotary evaporator
  4. extractionthe residue extracted with methylene chloride
  5. dry with materialThe extract is dried with MgSO4
  6. customthe solvent is again removed on the rotary evaporator
  7. customto yield the product

Sources & evidence

ORD record
ord-bd7ddee354044392b7d9546781f462db
Source dataset
uspto-grants-1991_05
Patent number
US05019611

Linked notes

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