Allylamine → 3-((Prop-2-en-1-yl)sulfamoyl)benzoic acid

HRID 518642Notes

Reaction equation

HRID 518642 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].[CH2:14]([NH2:17])[CH:15]=[CH2:16].[OH-].[Na+]>C1COCC1.Cl>[CH2:14]([NH:17][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])[CH:15]=[CH2:16]

Participants

6

Reactant 3

HCID 7853AllylamineHCID 14798Sodium HydroxideHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 2574683-((Prop-2-en-1-yl)sulfamoyl)benzoic acidYield 95.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(chlorosulfonyl)benzoic acid (5 g, 22.66 mmol) in THF (50.4 mL) at 0° C. was added allylamine (2.038 mL, 27.2 mmol) followed by NaOH (1N aqueous) (49.9 mL, 49.9 mmol). The mixture was allowed to warm to RT over 1 hour and stirred an additional 16 hours. The mixture was diluted with 1N HCl (250 mL), and the aqeuous layer was extracted with EtOAc (300 mL). The organic layer was dried over sodium sulfate and concentrated to dryness to afford 3-(N-allylsulfamoyl)benzoic acid as white solid (5.2 g, 95% yield). MS m/z=242.0 [M+H]. Calc'd for C10H11NO4S: 241.0.

Workup

  1. extractionthe aqeuous layer was extracted with EtOAc (300 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-49a46971595040cf8faba1ce531b31fa
Source dataset
uspto-grants-2015_08
Patent number
US09115127B2

Reaction notes

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