1,1'-Carbonyldiimidazole → 2-Chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamide

HRID 2298058Notes

Reaction equation

HRID 2298058 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.[C:24]12([CH2:34][NH2:35])[CH2:33][CH:28]3[CH2:29][CH:30]([CH2:32][CH:26]([CH2:27]3)[CH2:25]1)[CH2:31]2>CN(C)C=O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][C:3]=1[C:4]([NH:35][CH2:34][C:24]12[CH2:33][CH:28]3[CH2:27][CH:26]([CH2:32][CH:30]([CH2:29]3)[CH2:31]1)[CH2:25]2)=[O:6]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 4582102-Chloro-5-hydroxybenzoic acid

Product 1

HCID 227314932-Chloro-5-hydroxy-N-(tricyclo[3.3.1.13,7]dec-1-ylmethyl)-benzamideYield 2.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-5-hydroxybenzoic acid (3.12 g) in N,N-dimethylformamide (50 ml) was added 1,1′-carbonyldiimidazole (3.0 g). The resulting reaction mixture was stirred for 2.5 h and then 1-adamantanemethylamine (3.0 g) was added. Stirring was continued for 14 h. The reaction mixture was partitioned between ethyl acetate and water and the organic layer was separated, washed with water and brine and then dried over sodium sulphate (Na2SO4). The organic layer was concentrated under reduced pressure to give a residue which was purified by silica gel chromatography (eluting with 3-10% methanol in dichloromethane) to yield the subtitle compound as a white solid (0.15 g).

Workup

  1. customThe resulting reaction mixture
  2. stirringStirring
  3. waitwas continued for 14 h
  4. customThe reaction mixture was partitioned between ethyl acetate and water
  5. customthe organic layer was separated
  6. washwashed with water and brine
  7. dry with materialdried over sodium sulphate (Na2SO4)
  8. concentrationThe organic layer was concentrated under reduced pressure
  9. customto give a residue which
  10. customwas purified by silica gel chromatography (eluting with 3-10% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7c04e8e063084f438f946ddf17236d16
Source dataset
uspto-grants-2002_12
Patent number
US06492355B1

Reaction notes

Loading…