Isopropyl iodide → Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoate

HRID 1288714Notes

Reaction equation

HRID 1288714 reaction equation
[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9](SC#N)=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[S-2:16].[Na+].[Na+].I[CH:20]([CH3:22])[CH3:21]>C(O)C.O>[NH2:1][C:2]1[C:3]([CH3:15])=[C:4]([C:9]([S:16][CH:20]([CH3:22])[CH3:21])=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6]

Participants

6

Reactant 3

HCID 6362Isopropyl iodideHCID 14804Sodium SulfideHCID 14801188Methyl 3-amino-2-methyl-6-thiocyanatobenzoate

Product 1

HCID 54177219Methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoateYield 75.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A suspension of methyl 3-amino-2-methyl-6-thiocyanatobenzoate (22.2 g) in ethanol was added to a solution of sodium sulphide (26.6 g) in water. The resultant mixture was stirred at room temperature for 1 hour and then cooled to 5° C. 2-Iodopropane (19.36 g) was added and the mixture was allowed to warm to room temperature and stirred for 2 hours. It was evaporated to dryness and the residue was suspended in aqueous sodium chloride solution and extracted with dichloromethane. The organic layer was dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)benzoate (18 g) as a yellow oil NMR(CDCl3) 1.2(d,6H) 2.0(s,3H) 3.0(m,1H) 3.8(bs,2H) 3.9(s,1H) 6.5(d,1H) 7.0(d,1H).

Workup

  1. temperatureto warm to room temperature
  2. customIt was evaporated to dryness
  3. extractionextracted with dichloromethane
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-2facbc2a476e4873862188ab8c3c6792
Source dataset
uspto-grants-1998_05
Patent number
US05747424

Reaction notes

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