Methyl iodide → HCID 86658458, compound

HRID 330857Notes

Reaction equation

HRID 330857 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

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 86658459HCID 86658459, compound

Product 1

HCID 86658458HCID 86658458, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Potassium carbonate (177 mg, 1.28 mmol), DMF (2 ml) and MeI (60 ml) were added to the compound (230 mg, 0.65 mmol) obtained in Step 1. The mixture was stirred at 40° C. for 6 hours. Potassium carbonate (44.3 mg) and MeI (40 μL) were supplemented and stirred overnight. After the solvent was removed by distillation, the purification step A was applied 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 purification step A was applied to give the crude product of 3-(methylamino)benzenesulfonic acid (84.1 mg).

Workup

  1. stirringstirred overnight
  2. customAfter the solvent was removed by distillation
  3. customthe purification step A

Sources & evidence

ORD record
ord-c7232f6b4b6e4c279d78571e7bb8f9db
Source dataset
uspto-grants-2014_11
Patent number
US08877739B2

Reaction notes

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