Dicyclohexylcarbodiimide → HCID 14182508, compound

HRID 1252621Notes

Reaction equation

HRID 1252621 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11]([C:23]([OH:25])=O)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C2N=NNC=2C=CC=1.[NH2:36][N:37]1[CH2:42][CH2:41][NH:40][C:39](=[O:43])[C:38]1=[O:44].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[O:44]=[C:38]1[C:39](=[O:43])[NH:40][CH2:41][CH2:42][N:37]1[NH:36][C:23]([C:11]1[CH:10]=[C:9]([O:8][CH2:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[CH:13][N:12]=1)=[O:25]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 141825074,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acidHCID 221847681-Aminopiperazine-2,3-dioneHCID 178418300HCID 178418300, compound

Product 1

HCID 14182508HCID 14182508, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid (7.1 g, 21.17 mmol), hydroxybenzotriazole (0.29 g, 2.12 mmol) and N-aminopiperazine-2,3-dione (2.73 g, 21.17 mmol) in 140 ml of dry dimethylformamide was added, after 15 minutes of stirring, 4.80 g (23.3 mmol) of dicyclohexylcarbodiimide. After stirring for 21 hours at room temperature, dicyclohexylurea was filtered off (4.0 g ) and the solvent was evaporated in vacuo. The solid residue was triturated for 40 minutes with 240 ml of tetrahydrofuran, filtered, washed with tetrahyrofuran and dried in vacuo to yield 7.76 g of the title compound, melting point 231.1° C.

Workup

  1. additionwas added, after 15 minutes
  2. stirringAfter stirring for 21 hours at room temperature
  3. filtrationdicyclohexylurea was filtered off (4.0 g )
  4. customthe solvent was evaporated in vacuo
  5. customThe solid residue was triturated for 40 minutes with 240 ml of tetrahydrofuran
  6. filtrationfiltered
  7. washwashed with tetrahyrofuran
  8. customdried in vacuo

Sources & evidence

ORD record
ord-81ed4b1db5334fe3bea74590afbf00bf
Source dataset
uspto-grants-1988_05
Patent number
US04743685

Reaction notes

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