Triethylamine → 3-Amino-4-methoxy-benzenesulfonic acid 3,4,5-trimethoxy-phenyl ester

HRID 1059839Notes

Reaction equation

HRID 1059839 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([OH:13])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].C(N(CC)CC)C.[CH3:21][O:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](F)(=[O:31])=[O:30])=[CH:25][C:24]=1[NH2:33].[I-].C([NH3+])(C)(C)C>ClCCl>[NH2:33][C:24]1[CH:25]=[C:26]([S:29]([O:13][C:5]2[CH:6]=[C:7]([O:11][CH3:12])[C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)(=[O:31])=[O:30])[CH:27]=[CH:28][C:23]=1[O:22][CH3:21]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 695053,4,5-TrimethoxyphenolHCID 969523-Amino-4-methoxyphenylsulphonyl fluorideHCID 22344722t-Butylammonium Iodide

Product 1

HCID 98206553-Amino-4-methoxy-benzenesulfonic acid 3,4,5-trimethoxy-phenyl esterYield 35%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3,4,5-trimethoxyphenol (505.7 mg, 2.75 mmol) in dichloromethane (28 mL) was treated sequentially with triethylamine (1.2 mL), 4-methoxymetanilyl fluoride (572.5 mg, 2.75 mmol), and tert-butylammonium iodide (106 mg, 0.287 mmol), stirred overnight, and washed once with 1M Na2CO3. The organic layer was separated, dried (MgSO4), filtered, and concentrated. Chromatography of the concentrate on silica gel with 40% ethyl acetate/hexanes provided 356 mg of the desired compound.

Workup

  1. washwashed once with 1M Na2CO3
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. concentrationChromatography of the concentrate on silica gel with 40% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-3462e9bbd0674957b0e4a1b6e9cb8fd0
Source dataset
uspto-grants-2003_02
Patent number
US06521658B1

Reaction notes

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