Dicyclohexylcarbodiimide → HCID 14182468, compound

HRID 1252603Notes

Reaction equation

HRID 1252603 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[O:16]=[C:17]1[C:22]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:21][NH:20][C:19]([C:31]([OH:33])=O)=[CH:18]1.[C:34]([O:38][CH2:39][C:40]1[CH:45]=[CH:44][C:43]([O:46][CH3:47])=[CH:42][CH:41]=1)(=[O:37])[NH:35][NH2:36].O.ON1C2C=CC=CC=2N=N1>CN(C)C1C=CN=CC=1.CN(C)C=O>[CH3:47][O:46][C:43]1[CH:42]=[CH:41][C:40]([CH2:39][O:38][C:34]([NH:35][NH:36][C:31]([C:19]2[NH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:17](=[O:16])[CH:18]=2)=[O:33])=[O:37])=[CH:45][CH:44]=1

Participants

7

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 87847p-Methoxybenzyl carbazateHCID 27960291-Hydroxybenzotriazole hydrateHCID 110539185-(Benzyloxy)-4-oxo-1,4-dihydropyridine-2-carboxylic acid

Product 1

HCID 14182468HCID 14182468, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

A solution of 4.54 g (0.022 moles) dicyclohexylcarbodiimide in 25 ml dry of dimethylformamide was added to a stirred suspension of 4.90 g (0.020 moles) of 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 4.50 g (0.022 moles) of 4-methoxybenzyl carbazate, 0.12 g (1.0 mmol) of 4-dimethylamino-pyridine and 0.155 g (1.0 mmol) of 1-hydroxybenzotriazole hydrate in 25 ml of dry dimethylformamide at room temperature and stirring was continued overnight. The precipitate was filtered off and the filtrate was evaporated in vacuo. The residue solidified by stirring with ether and aqueous sodium bicarbonate and the solid was collected, washed with water and finally dried in vacuo. The crude material (8.14 g) was extracted in a soxhlet-apparatus with 800 ml CHCl3 (7 hours). 5.70 g (67%) of pure 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[[(4-methoxyphenyl)methoxy]carbonyl]hydrazide crystallized directly from the cold CHCl3 -extract, and an additional impure amount (1.5 g, 18%) of the title compound could be obtained by evaporation of the CHCl3 -solution in vacuo; melting point 174.5°-178° C.

Workup

  1. filtrationThe precipitate was filtered off
  2. customthe filtrate was evaporated in vacuo
  3. stirringby stirring with ether and aqueous sodium bicarbonate
  4. customthe solid was collected
  5. washwashed with water
  6. customfinally dried in vacuo
  7. extractionThe crude material (8.14 g) was extracted in a soxhlet-apparatus with 800 ml CHCl3 (7 hours)
  8. custom5.70 g (67%) of pure 1,4-dihydro-4-oxo-5-(phenylmethoxy)-2-pyridinecarboxylic acid, 2-[[(4-methoxyphenyl)methoxy]carbonyl]hydrazide crystallized directly from the cold CHCl3 -extract

Sources & evidence

ORD record
ord-b272f6d4d610481ba6d731a7cde24d35
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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