Iodine → N-(tert-butyl)-2-iodo-6-methoxybenzenesulfonamide

HRID 2264125Notes

Reaction equation

[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[I:22]I>O1CCCC1>[C:1]([NH:5][S:6]([C:9]1[C:10]([O:15][CH3:16])=[CH:11][CH:12]=[CH:13][C:14]=1[I:22])(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: -30 °C

Procedure

A solution of 30.00 g (123.29 mmol) of N-(tert-butyl)-2-methoxybenzenesulfonamide in 400 ml of tetrahydrofuran is cooled to −70° C. and slowly admixed with a solution of 110.96 ml (277.41 mmol) of a 2.5 molar n-butyllithium solution in THF. The solution is subsequently warmed briefly to −30° C. and then cooled again to −60° C. At this temperature a solution of 31.29 g (123.29 mmol) of iodine in 200 ml of tetrahydrofuran is added dropwise. Subsequently the reaction solution is stirred at room temperature overnight. Following extraction with water, the organic phase is dried over sodium sulfate and evaporated to dryness. This gives 42.40 g (93% of theory) of N-(tert-butyl)-2-iodo-6-methoxybenzenesulfonamide.

Workup

temperaturecooled again to −60° C
extractionextraction with water
dry with materialthe organic phase is dried over sodium sulfate
customevaporated to dryness

Sources & evidence

ORD record: ord-3f93c616012f444e9f01790214c63b9c
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855166B2

Reaction notes

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