1-Bromooctane → 3-Formyl-2-[(4-methoxy-benzenesulfonyl)-octyl-amino]-benzoic acid methyl ester

HRID 583384Notes

Reaction equation

HRID 583384 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[NH:12][S:13]([C:16]1[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=1)(=[O:15])=[O:14].[H-].[Na+].[CH2:27](Br)[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]>CN(C=O)C.CCOCC>[CH3:1][O:2][C:3](=[O:24])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH:10]=[O:11])[C:5]=1[N:12]([S:13]([C:16]1[CH:17]=[CH:18][C:19]([O:22][CH3:23])=[CH:20][CH:21]=1)(=[O:14])=[O:15])[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34]

Participants

6

Reactant 3

HCID 81401-BromooctaneHCID 24758Sodium hydrideHCID 543619953-Formyl-2-(4-methoxy-benzenesulfonylamino)-benzoic acid methyl ester

Product 1

HCID 867543143-Formyl-2-[(4-methoxy-benzenesulfonyl)-octyl-amino]-benzoic acid methyl esterYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.0 g (2.865 mmol) of the product of Example 321 in 7.5 mL of DMF was added 0.143 g (3.582 mmol) of 60% sodium hydride followed by 0.74 mL (4.30 mmol) of n-octyl bromide. The reaction was stirred overnight at room temperature then diluted with ether, washed with water, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was chromatographed on silica gel eluting with EtOAc/hexanes (1:3) to provide 0.592 g (49%) of the product as a white solid. Electrospray Mass Spec: 462.1 (M+H)+.

Workup

  1. washwashed with water
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was chromatographed on silica gel eluting with EtOAc/hexanes (1:3)

Sources & evidence

ORD record
ord-fb003c3b913a4a798aaa53e08cc07606
Source dataset
uspto-grants-1999_07
Patent number
US05929097

Reaction notes

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