Potassium Iodide → Methyl 3-iodo-2-methyl-6-(1-methylethylsulphenyl)benzoate
Reaction equation
N([O-])=O.[Na+].N[C:6]1[C:7]([CH3:20])=[C:8]([C:13]([S:16][CH:17]([CH3:19])[CH3:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10].[I-:21].[K+]>O.Cl>[I:21][C:6]1[C:7]([CH3:20])=[C:8]([C:13]([S:16][CH:17]([CH3:19])[CH3:18])=[CH:14][CH:15]=1)[C:9]([O:11][CH3:12])=[O:10]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 80 °C
Procedure
A solution of sodium nitrite (6.7 g) in water was added to a stirred, cooled mixture of methyl 3-amino-2-methyl-6-(1-methylethylsulphenyl)-benzoate (18 g) in concentrated hydrochloric acid while maintaining the temperature below 0° C. The resultant mixture was added to a solution of potassium iodide (16 g) in water while maintaining the temperature at about 80° C. The resultant mixture was stirred at 80° C. for 15 mins then cooled to room temperature. It was diluted with water and extracted with dichloromethane. The organic layer was washed with sodium bicarbonate solution, water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give methyl 3-iodo-2-methyl-6-(1-methylethylsulphenyl)benzoate (20.5 g) as a red oil. NMR (CDCl3) 1.25 (d,6H) 2.35(s,3H) 3.2(m, 1H) 3.9(s,3H) 6.9(d, 1H) 7.6(d, 1H).
Workup
- temperaturecooled
- temperaturewhile maintaining the temperature below 0° C
- temperaturethen cooled to room temperature
- extractionextracted with dichloromethane
- washThe organic layer was washed with sodium bicarbonate solution, water
- dry with materialdried (MgSO4)
- filtrationfiltered
- customThe filtrate was evaporated to dryness
Sources & evidence
- ORD record
- ord-12e10774a21f48e9ac5e2890c8b4f7d8
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05656573
Reaction notes
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