4-Fluorobenzoic Acid → N-[(dimethylamino)sulfonyl]-4-fluorobenzamide

HRID 1525663Notes

Reaction equation

HRID 1525663 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](O)=[O:7])=[CH:4][CH:3]=1.C[CH2:12][N:13]=[C:14]=NCCCN(C)C.C(N(CC)C(C)C)(C)C.CN[N:33](NC)[SH:34](=[O:36])=[O:35]>ClCCCl.CN(C1C=CN=CC=1)C.O.Cl>[CH3:12][N:13]([CH3:14])[S:34]([NH:33][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:2]([F:1])=[CH:3][CH:4]=1)(=[O:36])=[O:35]

Participants

9

Reactant 4

HCID 99734-Fluorobenzoic AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 178486254HCID 178486254, compound

Product 1

HCID 47363087N-[(dimethylamino)sulfonyl]-4-fluorobenzamideYield 47.5%

Reagents, catalysts & solvents 4

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolventHCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Procedure

To a solution of 4-fluorobenzoic acid (700 mg, 5.0 mmol) in 1,2-dichloroethane (30 mL) was added EDCI (2.38 g, 12.5 mmol), DMAP (1.52 mg, 12.5 mmol) and N,N-diisopropylethylamine (2.17 mL, 12.5 mmol) and stirred for 20 minutes at room temperature. N,N-dimethylaminosulfonamide (1.24 g, 10.0 mmol) was added to the solution and the mixture heated at 60° C. for 2.5 hours. The mixture was cooled, diluted with water (20 mL) and 2M HCl (20 mL) and extracted with DCM (3×30 mL), washed with water (20 mL) and dried over MgSO4. The solvent was removed in vacuo to afford the title compound as a white solid (585 mg, 47%). No further purification was necessary.

Workup

  1. temperaturethe mixture heated at 60° C. for 2.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with DCM (3×30 mL)
  4. washwashed with water (20 mL)
  5. dry with materialdried over MgSO4
  6. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-bbd062d508f34b269d617fa103a14872
Source dataset
uspto-grants-2015_07
Patent number
US09085517B2

Reaction notes

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