Hydrochloric Acid → 4-Methyl-5-iodosaccharin

HRID 810

Reaction equation

Cl.[CH3:2][C:3]1[C:13](N)=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8].N([O-])=O.[Na+].[I-:20].[K+]>O.C(O)(=O)C>[CH3:2][C:3]1[C:13]([I:20])=[CH:12][CH:11]=[C:10]2[C:4]=1[C:5](=[O:15])[NH:6][S:7]2(=[O:9])=[O:8]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of 205 ml of glacial acetic acid, 160 ml of water and 40 ml of conc. HCl is initially taken and 23.4 g (0.11 mol) of 4-methyl-5-aminosaccharin are introduced with stirring at 15°-20° C. 7.9 g (0.115 mol) of sodium nitrite are added dropwise to the resulting suspension at 5°-10° C. and it is stirred at 5° C. for 30 min. The diazonium salt, which is present as a suspension, is then added dropwise in portions to a solution of 19.1 g (0.115 mol) of potassium iodide in 170 ml of water which is warmed to 50° C., nitrogen being formed. After cooling to room temperature, the deposited product is isolated by filtering off with suction, washed with water and dried under reduced pressure at 50° C. 32.5 g (0.1 mol=91% of theory) of a solid of m.p.: 257°-258° C. are obtained. A combustion analysis gave an iodine content of 38.5% (theory 39.3%).

Workup

stirringit is stirred at 5° C. for 30 min
customnitrogen being formed
temperatureAfter cooling to room temperature
customthe deposited product is isolated
filtrationby filtering off with suction
washwashed with water
customdried under reduced pressure at 50° C
custom32.5 g (0.1 mol=91% of theory) of a solid of m.p.: 257°-258° C. are obtained

Sources & evidence

ORD record: ord-64895c5b03224120a7cbd0bc650559fc
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05723415

Linked notes

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