Sodium hydride → HCID 11091303, compound

HRID 1386028Notes

Reaction equation

HRID 1386028 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5](=[O:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12](=[O:25])(=[O:24])[NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:22])[F:21].Br[CH2:28][C:29]([O:31][CH3:32])=[O:30]>CN(C=O)C>[CH3:3][O:4][C:5](=[O:26])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[S:12](=[O:25])(=[O:24])[N:13]([CH2:28][C:29]([O:31][CH3:32])=[O:30])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]([F:23])([F:21])[F:22]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10981234Benzoic acid, 2-[[[2-(trifluoromethyl)phenyl]amino]sulfonyl]-, methyl ester

Product 1

HCID 11091303HCID 11091303, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To the suspension of NaH (60% in mineral oil, 2.0 g, 50 mmol) in 45 mL of DMF at 0° C. was added a solution of 2-(2-trifluoromethyl-phenylsulfamoyl)-benzoic acid methyl ester (12.0 g, 33.3 mmol) in 22 mL of DMF dropwise. After about 10 minutes, 11.22 g (66.8 mmol) of methyl bromoacetate was added, and reaction solution was warmed to room temperature in 3 hours. The light yellow reaction mixture was poured into ice water. The mixture was then extracted with EtOAc 3×(˜400 mL) and washed with brine. The organic layer was dried over MgSO4 and evaporated down to a sick light orange oil. White crystals were formed upon treatment with Et2O and hexane. It was collected and dried over the vacuum oven to give pure 2-[methoxycarbonylmethyl-(2-trifluoromethyl-phenyl)-sulfamoyl]-benzoic acid methyl ester (13.85 g, 96%).

Workup

  1. customreaction solution
  2. extractionThe mixture was then extracted with EtOAc 3×(˜400 mL)
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated down to a sick light orange oil
  6. customWhite crystals were formed upon treatment with Et2O and hexane
  7. customIt was collected
  8. customdried over the vacuum oven

Sources & evidence

ORD record
ord-9328ecc2242d4911a9ba47cabbcc5ca6
Source dataset
uspto-grants-2001_07
Patent number
US06265399B1

Reaction notes

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