Dimethylformamide → HCID 15570210, compound

HRID 2402925Notes

Reaction equation

HRID 2402925 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7]I.[N+](C1C=CC=CC=1S([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)=O)([O-])=O.[C:32](=[O:35])([O-])[O-].[Cs+].[Cs+].[C:38]1(S)C=CC=C[CH:39]=1.[CH3:45][N:46]([CH:48]=O)C>>[CH3:7][N:21]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([OH:31])(=[O:29])=[O:30])[CH:23]=1)[C:32](=[O:35])[CH2:38][CH2:39][C@@H:48]([C:1]([OH:2])=[O:4])[NH2:46].[CH3:45][NH:21][C:22]1[CH:23]=[C:24]([S:28]([OH:31])(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1

Participants

8

Reactant 6

HCID 6228Dimethylformamide2×HCID 6328Methyl iodide2×HCID 7969ThiophenolHCID 10796Cesium carbonateHCID 11430Potassium Carbonate2×HCID 86658459HCID 86658459, compound

Product 2

HCID 15570210HCID 15570210, compoundHCID 123242112HCID 123242112, compound

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, and stirred at 40° C. for 6 hours. Potassium carbonate (44.3 mg) and MeI (40 μL) were further added thereto and stirred overnight. After removing a solvent, purification was conducted in accordance with the purification process A to obtain a crude product (160 mg) of 3-{methyl[(2-nitrophenyl)sulfonyl]amino}benzenesulfonic acid. The crude product (144 mg, 0.39 mmol) was dissolved in DMF (3 mL), and cesium carbonate (126 mg, 0.39 mmol) and thiophenol (40 μL, 0.39 mmol) were added thereto and stirred at 50° C. overnight. After removing a solvent, purification was conducted in accordance with the purification process A to obtain to a crude product (84.1 mg) of 3-(methylamino)benzenesulfonic acid. Then, a title compound was obtained by the same method as that of the synthetic example 1 except that the crude product of 3-(methylamino)benzenesulfonic acid was used instead of 3-sulfoaniline.

Workup

  1. stirringstirred overnight
  2. customAfter removing
  3. customa solvent, purification
  4. customA to obtain a crude product (160 mg) of 3-{methyl[(2-nitrophenyl)sulfonyl]amino}benzenesulfonic acid
  5. stirringstirred at 50° C. overnight
  6. customAfter removing
  7. customa solvent, purification
  8. customA to obtain to a crude product (84.1 mg) of 3-(methylamino)benzenesulfonic acid

Sources & evidence

ORD record
ord-a7f21da34ec84d928f46210c7fd512e1
Source dataset
uspto-grants-2014_08
Patent number
US08796485B2

Reaction notes

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