Tetrahydrofuran → 4-[3-(1-Adamantyl)-4-methoxybenzoyloxy]benzenesulfonamide

HRID 129674Notes

Reaction equation

HRID 129674 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14]([OH:16])=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O[C:23]1[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.C1COCC1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.O>[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14]([O:16][C:23]3[CH:28]=[CH:27][C:26]([S:29]([NH2:32])(=[O:31])=[O:30])=[CH:25][CH:24]=3)=[O:15])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 74093p-HydroxybenzenesulfonamideHCID 52965033-(1-Adamantyl)-4-methoxybenzoic acid

Product 1

HCID 148525094-[3-(1-Adamantyl)-4-methoxybenzoyloxy]benzenesulfonamideYield 46%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolvent

Procedure

Into a round bottom flask, there are introduced 2.86 g (10 mmoles) of 3-(1-adamantyl)-4-methoxybenzoic acid, 1.73 g (10 mmoles) of 4-hydroxybenzenesulfonamide and 50 ml of THF. There are added, successively, 2.1 g (10 mmoles) of 1,3-dicyclohexylcarbodiimide and then 1.22 (10 mmoles) of 4-dimethylaminopyridine. The medium is stirred at ambient temperature for 4 hours. The reaction medium is poured into water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting solid is purified by chromatography on a silica column eluted by a 60:40 mixture of ethyl ether and hexane. After evaporation of the solvents, 2 g (46% yield) of 4-[3-(1-adamantyl)-4-methoxybenzoyloxy]benzenesulfonamide having a melting point of 223°-224° C. are recovered.

Workup

  1. additionThere are added
  2. extractionextracted with ethyl ether
  3. customThe organic phase is decanted
  4. washwashed with water
  5. customdried on magnesium sulfate
  6. customevaporated
  7. customThe resulting solid is purified by chromatography on a silica column
  8. washeluted by a 60:40 mixture of ethyl ether and hexane

Sources & evidence

ORD record
ord-adfbc46c6fca49afa2549a254fac1eb5
Source dataset
uspto-grants-1995_11
Patent number
US05468897

Reaction notes

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