Water → HCID 58909952, compound

HRID 1296031Notes

Reaction equation

HRID 1296031 reaction equation
[CH3:1][NH:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH2:11][NH2:12])=[CH:6][C:5]=1[O:13][CH2:14][CH3:15].[N+:17]([C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)([O-:19])=[O:18].O.C(OCC)(=O)C>N1C=CC=CC=1>[CH3:1][NH:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([Br:10])[C:7]([CH2:11][NH:12][S:26]([C:23]2[CH:22]=[CH:21][C:20]([N+:17]([O-:19])=[O:18])=[CH:25][CH:24]=2)(=[O:27])=[O:28])=[CH:6][C:5]=1[O:13][CH2:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 74044-Nitrobenzenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 229297314-(Aminomethyl)-5-bromo-2-ethoxy-N-methylbenzamide

Product 1

HCID 58909952HCID 58909952, compoundYield 74.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

After dissolving the N1-methyl-4-(aminomethyl)-5-bromo-2-ethoxybenzamide (6.77 g) in pyridine (50 ml), 4-nitrobenzenesulfonyl chloride (5.3 g) was added and the mixture was stirred at room temperature overnight. Water and ethyl acetate were then added for separation. The organic layer was washed with 1 N hydrochloric acid and brine and the precipitated crystals were filtered out (5.57 g). The organic layer of the filtrate was dried over anhydrous magnesium sulfate, filtered and concentrated and the residue was washed with ethyl acetate and filtered. A total of 8.31 g of the title compound was obtained as a white solid.

Workup

  1. additionwas added
  2. washThe organic layer was washed with 1 N hydrochloric acid and brine
  3. filtrationthe precipitated crystals were filtered out (5.57 g)
  4. dry with materialThe organic layer of the filtrate was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washthe residue was washed with ethyl acetate
  8. filtrationfiltered

Sources & evidence

ORD record
ord-9317e747f399468d8d722818a7ccd915
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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