Oxalyl chloride → 4-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamide

HRID 1889672Notes

Reaction equation

HRID 1889672 reaction equation
[Cl:1][C:2]1[C:3]([OH:31])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([OH:28])=O)=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:11])=[O:10])[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:39][NH:40][O:41][CH3:42]>C(Cl)Cl.CN(C=O)C>[Cl:1][C:2]1[C:3]([OH:31])=[C:4]([S:9]([N:12]([CH2:21][C:22]2[CH:30]=[CH:29][C:25]([C:26]([N:40]([O:41][CH3:42])[CH3:39])=[O:28])=[CH:24][CH:23]=2)[CH2:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=2)(=[O:10])=[O:11])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 58531400HCID 58531400, compound

Product 1

HCID 585315364-((3,5-Dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)-N-methoxy-N-methylbenzamideYield 65.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 4-((3,5-dichloro-N-(4-fluorobenzyl)-2-hydroxyphenylsulfonamido)methyl)benzoic acid (0.726 g, 1.5 mmol) in DCM (20 mL) at rt was added oxalyl chloride (0.394 mL, 4.50 mmol) and a few drops of DMF. The mixture was stirred at rt to give a yellow solution. The reaction mixture was concentrated and the residue was dissolved in DCM. At 0° C., a mixture of N,O-dimethylhydroxylamine hydrochloride (0.439 g, 4.50 mmol) and TEA (1.045 mL, 7.50 mmol) were added. The resulting mixture was stirred at rt for 1 h. The mixture was diluted with DCM and washed with water and brine. The organic extract was dried, concentrated and purified by flash column chromatography (ISCO system, eluting with DCM/EtOAc) to give the desired product (0.516 g, 62%) as a light yellow solid. MS (ESI): 527.1 (M+H)+.

Workup

  1. customto give a yellow solution
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was dissolved in DCM
  4. additionwere added
  5. stirringThe resulting mixture was stirred at rt for 1 h
  6. washwashed with water and brine
  7. extractionThe organic extract
  8. customwas dried
  9. concentrationconcentrated
  10. custompurified by flash column chromatography (ISCO system, eluting with DCM/EtOAc)

Sources & evidence

ORD record
ord-c23f91aaf27f4d8c98e6ffb7c660787e
Source dataset
uspto-grants-2013_08
Patent number
US08501992B2

Reaction notes

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