2-Nitrobenzenesulfonyl chloride → HCID 178525722, compound

HRID 1840721Notes

Reaction equation

HRID 1840721 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10](Cl)(=[O:12])=[O:11])([O-:3])=[O:2].[NH2:14][CH2:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([C:22]([OH:24])=[O:23])[CH2:18][CH2:17]1>O1CCOCC1.[OH-].[Na+]>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10]([NH:14][CH2:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([C:22]([OH:24])=[O:23])[CH2:20][CH2:21]1)(=[O:12])=[O:11])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 178511262HCID 178511262, compound

Product 1

HCID 178525722HCID 178525722, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 29.9 g (0.135 mol) of o-nitrobenzenesulfonyl chloride in 150 ml of dioxane and 150 ml of 1 N NaOH was added simultaneously and dropwise at 4° C. (ice bath) to a solution of 14.13 g (0.09 mol) of trans-4-(aminomethyl)cyclohexanecarboxylic acid in a two-phase system comprising 90 ml of 1 N NaOH and 90 ml of dioxane. After the slightly exothermic reaction had died down, stirring was carried out for 30 minutes at room temperature, the precipitate which separated out was filtered off with suction and washed with a little ice water and the filtrate was evaporated down under reduced pressure, further precipitation of salt occurring. The combined amounts of salt were digested with ether, suspended in water, acidified with 1 M KHSO4 solution and extracted with ethyl acetate. The ethyl acetate phase was washed with sodium chloride solution, dried over Na2SO4 and evaporated down under reduced pressure.

Workup

  1. customAfter the slightly exothermic reaction
  2. customthe precipitate which separated out
  3. filtrationwas filtered off with suction
  4. washwashed with a little ice water
  5. customthe filtrate was evaporated down under reduced pressure, further precipitation of salt
  6. extractionextracted with ethyl acetate
  7. washThe ethyl acetate phase was washed with sodium chloride solution
  8. dry with materialdried over Na2SO4
  9. customevaporated down under reduced pressure

Sources & evidence

ORD record
ord-967d8b35e55f40e982291b6cb4d11e4f
Source dataset
uspto-grants-2004_01
Patent number
US06683055B1

Reaction notes

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