Triethylamine → HCID 67044384, compound

HRID 1944391Notes

Reaction equation

HRID 1944391 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][C:5]([NH:6]C)=[CH:4][CH:3]=1.[CH2:10]([N:12](CC)CC)C.[CH3:17][O:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](Cl)(=[O:28])=[O:27]>ClCCl>[NH3:6].[CH3:17][O:18][C:19](=[O:30])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[S:26](=[O:28])(=[O:27])[NH:12][CH2:10][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:9][CH:8]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 680244-Fluoro-N-methylanilineHCID 117830Benzoic acid, 2-(chlorosulfonyl)-, methyl ester

Product 2

HCID 222AmmoniaHCID 67044384HCID 67044384, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-fluoro-N-methylaniline (0.53 g), triethylamine (0.65 g) and dichloromethane (2.0 mL) was treated with 2-chlorosulfonylbenzoic acid methyl ester (1.0 g), and the resulting mixture was stirred at room temperature for 24 hours. The mixture was partitioned between water and dichloromethane, and the organic phase was washed with saturated aqueous sodium chloride solution and dried over sodium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on SCX-2, eluting with methanol and then 2.0 M ammonia in methanol to afford the title compound as a pale yellow solid (1.2 g).

Workup

  1. customThe mixture was partitioned between water and dichloromethane
  2. washthe organic phase was washed with saturated aqueous sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on SCX-2
  6. washeluting with methanol

Sources & evidence

ORD record
ord-24251733ba2a4c1ebb9efb03f266d448
Source dataset
uspto-grants-2013_03
Patent number
US08394836B2

Reaction notes

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