Methyl iodide → HCID 54000078, compound

HRID 1612644Notes

Reaction equation

[C:1](=[O:4])([O-])[O-].[K+].[K+].Cl[C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:14]([N+:20]([O-:22])=[O:21])=[CH:13][C:9]=1[C:10](O)=O.[CH:23]([SH:26])([CH3:25])C.[CH3:27]I>CN(C)C=O>[CH3:1][O:4][C:23](=[S:26])[C:25]1[CH:8]=[C:16]([N+:17]([O-:19])=[O:18])[CH:15]=[C:14]([N+:20]([O-:22])=[O:21])[C:13]=1[CH:9]([CH3:10])[CH3:27]

Participants

Conditions

Temperature: -5 °C

Procedure

33.2 g (0.240 mol) of potassium carbonate are introduced into 100 ml of dimethylformamide and cooled to -5° C. 37.5 g (0.114 mol) of 2-chloro-3,5-dinitrobenzoic acid (75% with 25% water) in 110 ml of dimethylformamide are then added over a period of 20 minutes, during which time the internal temperature is maintained at from -7° to -3° C. 11.0 ml (0.114 mol) of isopropyl mercaptan (97%) in 20 ml of dimethylformamide are then added dropwise at from -8° to -1° C. over a period of 45 minutes. The batch is then stirred for one hour at 0° C. and the temperature is then raised to 25° C. over a period of 24 hours. 7.5 ml (0.12 mol) of methyl iodide are then added dropwise at room temperature over a period of 30 minutes. The reaction mixture is subsequently stirred for 16 hours at room temperature and then poured onto 500 ml of ice/water, stirred and filtered. The material obtained by filtering with suction is washed with water and dried at room temperature.

Workup

temperatureis maintained at from -7° to -3° C
temperaturethe temperature is then raised to 25° C. over a period of 24 hours
stirringThe reaction mixture is subsequently stirred for 16 hours at room temperature
stirringstirred
filtrationfiltered
customThe material obtained
filtrationby filtering with suction
washis washed with water
customdried at room temperature

Sources & evidence

ORD record: ord-800060c69f764617b05e0d2ed55246cd
Source dataset: uspto-grants-1993_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05190928

Reaction notes

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