tert-Butyl methyl ether → 1-Formyl-n-(3,4,5-trimethoxyphenyl)-5-indolinesulfonamide

HRID 50120Notes

Reaction equation

HRID 50120 reaction equation
[CH:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12](Cl)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=[O:2].[CH3:16][O:17][C:18]1[CH:19]=[C:20]([CH:22]=[C:23]([O:27][CH3:28])[C:24]=1[O:25][CH3:26])[NH2:21].C(=O)(O)[O-].[Na+].C(OC)(C)(C)C>C(OCC)(=O)C.O>[CH:1]([N:3]1[C:11]2[C:6](=[CH:7][C:8]([S:12]([NH:21][C:20]3[CH:22]=[C:23]([O:27][CH3:28])[C:24]([O:25][CH3:26])=[C:18]([O:17][CH3:16])[CH:19]=3)(=[O:14])=[O:13])=[CH:9][CH:10]=2)[CH2:5][CH2:4]1)=[O:2]

Participants

7

Reactant 4

HCID 15413tert-Butyl methyl etherHCID 322853,4,5-TrimethoxyanilineHCID 516892Sodium BicarbonateHCID 104219941-formyl-2,3-dihydro-1H-indole-5-sulfonyl chloride

Product 1

HCID 102939101-Formyl-n-(3,4,5-trimethoxyphenyl)-5-indolinesulfonamideYield 95,677.102%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A room temperature mixture of Example 1 (153.5 g, 0.625 mol), 3,4,5-trimethoxyaniline (109 g, 0.595 mmol), and sodium bicarbonate (75 g, 0.895 mol) in ethyl acetate (1.1 L) and water (1.05 L) was stirred for 20 hours, treated with methyl tert-butyl ether (1 L), stirred for 1 hour, filtered, washed with water (2×500 mL) and methyl tert-butyl ether (2×300 mL), and dried under vacuum at 50° C. for 20 hours to provide 223.4 g of the desired product (95.7%) as a mixture of rotamers.

Workup

  1. filtrationfiltered
  2. washwashed with water (2×500 mL) and methyl tert-butyl ether (2×300 mL)
  3. customdried under vacuum at 50° C. for 20 hours

Sources & evidence

ORD record
ord-042d32e9de264a3497b4be9e20b9833a
Source dataset
uspto-grants-2004_03
Patent number
US06710185B2

Reaction notes

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