Methyl iodide → HCID 86658458, compound

HRID 1468311Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[CH3:7]I.[N+:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[S:18]([NH:21][C:22]1[CH:23]=[C:24]([S:28]([OH:31])(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1)(=[O:20])=[O:19])([O-:11])=[O:10]>CN(C=O)C>[CH3:7][N:21]([S:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[N+:9]([O-:11])=[O:10])(=[O:20])=[O:19])[C:22]1[CH:23]=[C:24]([S:28]([OH:31])(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Potassium carbonate (177 mg, 1.28 mmol), DMF (2 ml) and MeI (60 μl) were added to the compound (230 mg, 0.65 mmol) obtained in Step 1, followed by stirring at 40° C. for 6 hours. Potassium carbonate (44.3 mg) and MeI (40 μL) were supplemented and the mixture was stirred overnight. After the solvent was removed by distillation, the mixture was purified according to the purification step A to give the crude product of 3-{methyl[(2-nitrophenyl)sulfonyl]amino}benzenesulfonic acid (160 mg). This crude product (144 mg, 0.39 m ml) was dissolved in DMF (3 ml), and cesium carbonate (126 mg, 0.39 mmol) and thiophenol (40 μl, 0.39 mmol) were added to the solution. The mixture was stirred at 50° C. overnight. After the solvent was removed by distillation, the mixture was purified in accordance with the purification step A to give the crude product of 3-(methylamino)benzenesulfonic acid (84.1 mg).

Workup

stirringthe mixture was stirred overnight
customAfter the solvent was removed by distillation
customthe mixture was purified
customaccording to the purification step A

Sources & evidence

ORD record: ord-3de7552e4c5645079709097b3290ad53
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000208B2

Reaction notes

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