Benzenesulfonyl chloride → HCID 178525721, compound

HRID 1797005Notes

Reaction equation

HRID 1797005 reaction equation
[NH2:1][CH2:2][C@H:3]1[CH2:8][CH2:7][C@H:6]([C:9]([OH:11])=[O:10])[CH2:5][CH2:4]1.[OH-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>O>[C:14]1([S:20]([NH:1][CH2:2][C@H:3]2[CH2:4][CH2:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][CH2:8]2)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 178511262HCID 178511262, compound

Product 1

HCID 178525721HCID 178525721, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

trans-4-(Aminomethyl)cyclohexane carboxylic acid (15.2 g, 0.097 mol) was dissolved in a 2N NaOH solution (96.5 mL, 2 equivalents). The solution was brought to 10° C., benzenesulfonyl chloride (17.1 g, 0.097 mol) was added dropwise and then the mixture was stirred overnight at room temperature. The mixture was diluted with water, the solution was washed with ether, and then the aqueous portion was acidified with 12N HCl to give an oily precipitate. The precipitate was extracted with CH2Cl2, and the extracts were dried (Na2SO4) and concentrated under reduced pressure to give trans-4-(Benzenesulfonylamino-methyl)-cyclohexanecarboxylic acid as a white solid.

Workup

  1. customwas brought to 10° C.
  2. washthe solution was washed with ether
  3. customto give an oily precipitate
  4. extractionThe precipitate was extracted with CH2Cl2
  5. dry with materialthe extracts were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-dd76f585c566482484e2705ec56cf2b1
Source dataset
uspto-grants-2006_04
Patent number
US07034034B2

Reaction notes

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