Benzoic Acid → HCID 18467634, compound

HRID 2229451Notes

Reaction equation

HRID 2229451 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([NH:14][S:15]([CH2:18][CH:19](O)[CH2:20][CH2:21][CH3:22])(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>O1CCCC1>[C:10]([NH:14][S:15]([CH2:18][CH:19]([O:8][C:1](=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:20][CH2:21][CH3:22])(=[O:17])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 243Benzoic AcidHCID 18467612HCID 18467612, compoundHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 18467634HCID 18467634, compoundYield 106.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Under nitrogen atmosphere, benzoic acid (92.8 g) was added gradually to a mixture of N,N′-carbonyldiimidazole (123.3 g) and tetrahydrofuran (500 ml) taking 10 minutes at room temperature. After stirring for 1 hour at room temperature, a solution of N-t-butyl-2-hydroxy-1-pentanesulfonamide (84.9 g) in tetrahydrofuran (300 ml) was added dropwise thereto taking 15 minutes. Then, a solution of diazabicycloundecene (57.9 g) in tetrahydrofuran (200 ml) was added dropwise thereto taking 35 minutes and the resulting solution was stirred for 17 hours at room temperature. The reaction mixture was decanted to ice-water, made acidic by adding dilute hydrochloric acid, and extracted with chloroform. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water, dried over sodium sulfate, and concentrated under reduced pressure to obtain N-t-butyl-2-benzoyloxy-1-pentanesulfonamide (132.8 g) as yellowish brown oil.

Workup

  1. waitthereto taking 15 minutes
  2. waitthereto taking 35 minutes
  3. stirringthe resulting solution was stirred for 17 hours at room temperature
  4. customThe reaction mixture was decanted to ice-water
  5. additionby adding dilute hydrochloric acid
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate and water
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-60cd37c4fd144095bd5d2b4b65c173a8
Source dataset
uspto-grants-2002_07
Patent number
US06420409B1

Reaction notes

Loading…