4720-73-4 → HCID 22493740, compound

HRID 1816418Notes

Reaction equation

HRID 1816418 reaction equation
C(C1NC=CN=1)(C1NC=CN=1)=O.[N:13]1([C:18]2[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=2[C:20]([OH:22])=O)[CH:17]=[CH:16][CH:15]=[N:14]1.[CH2:27]([NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:28]1[CH:36]=[CH:35][C:34]2[O:33][CH2:32][O:31][C:30]=2[CH:29]=1>O1CCCC1>[O:33]1[C:34]2[CH:35]=[CH:36][C:28]([CH2:27][N:37]([CH2:38][C:39]3[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=3)[C:20](=[O:22])[C:19]3[CH:23]=[CH:24][CH:25]=[CH:26][C:18]=3[N:13]3[CH:17]=[CH:16][CH:15]=[N:14]3)=[CH:29][C:30]=2[O:31][CH2:32]1

Participants

5

Reactant 3

HCID 7697924720-73-4HCID 47383832-Pyrazolylbenzoic acidHCID 5250894Bis-(1H-imidazol-2-YL)-methanone

Product 1

HCID 22493740HCID 22493740, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.1 equiv of carbonyl diimidazole is added to a solution of benzoic acid 178 (200 mg) in tetrahydrofuran (5 mL); the reaction is stirred at room temperature for 3 h. After this time N-piperonyl-N-benzylamine (0.25 g) is added in one portion. After 30 min, the reaction is filtered, diluted with ether and washed with water. The organic layer is dried (Na2SO4) and purified over column chromatography to provide the desired product (390 mg). The proton NMR displays a typically doubled pattern. 1H (CDCl3) 3.83 and 4.32 (two doublets, J=16 Hz, 1H), 3.91 (two doublets, J=8 Hz, 1H), 4.18 two doublets (J=6 Hz, 1H), 5.0 and 5.1 (two doublets, J=14 Hz, 1H), 5.93 and 5.98 (s and doublet, J=2 Hz, 2H, OCH2O), 6.35-6.40 (m, 2H), 6.51 (d, J=4 Hz, 0.5H), 6.4 (m, 1.5H), 7.0-7.88 m, 15H). LC-MS 412.3.

Workup

  1. waitAfter 30 min
  2. filtrationthe reaction is filtered
  3. additiondiluted with ether
  4. washwashed with water
  5. dry with materialThe organic layer is dried (Na2SO4)
  6. custompurified over column chromatography

Sources & evidence

ORD record
ord-e0b93687cfa648e3b5a1b35628c06fde
Source dataset
uspto-grants-2005_04
Patent number
US06884815B1

Reaction notes

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