HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 583928
Notes
Print preview

Reaction equation

HRID 583928 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6344
Dichloromethane
Solvent

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-1e4d61a307c34e5ab4b3ba24047a90d2
Source dataset
uspto-grants-2005_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06924304B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes