Dimethylamine → 3-(N,N-dimethylsulfamoyl)benzoic acid

HRID 1016190Notes

Reaction equation

HRID 1016190 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH3:14][NH:15][CH3:16].C1COCC1>C(Cl)Cl>[CH3:14][N:15]([CH3:16])[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 8028TetrahydrofuranHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 49857623-(N,N-dimethylsulfamoyl)benzoic acidYield 87%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(chlorosulfonyl)benzoic acid (152 mg, 0.689 mmol) in methylene chloride (2 mL) was treated with 2.0 M dimethylamine in THF (1.137 mL, 2.274 mmol), and the mixture was stirred overnight at room temperature. The reaction was quenched with 1 N HCl, and extracted 3× with EtOAc. The combined organic phases were washed with 1 N HCl followed by brine, then dried over sodium sulfate and concentrated in-vacuo to yield the title compound (138 mg, 0.602 mmol, 87% yield). MS (ESI+)=230.18, (M+H)+.

Workup

  1. customThe reaction was quenched with 1 N HCl
  2. extractionextracted 3× with EtOAc
  3. washThe combined organic phases were washed with 1 N HCl
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in-vacuo

Sources & evidence

ORD record
ord-ff8097910751497a8bf0bbbc0b01a8aa
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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