Dicyclohexylcarbodiimide → HCID 70375209, compound

HRID 980820Notes

Reaction equation

HRID 980820 reaction equation
Cl.[CH3:2][N:3]([CH3:8])[CH2:4][C:5](O)=[O:6].N[C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[CH:12][CH:11]=1.C1([N:30]=C=NC2CCCCC2)CCCCC1>O.CN(C)C=O>[CH3:2][N:3]([CH2:4][C:5]([C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:17]([CH3:23])[CH2:18][C:19](=[O:22])[NH:20][N:21]=2)=[C:12]([NH2:30])[CH:11]=1)=[O:6])[CH3:8]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 75605N,N-Dimethylglycine hydrochlorideHCID 161928Ici 109,081

Product 1

HCID 70375209HCID 70375209, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

In 1 ml of water was dissolved 0.7 g of N,N-dimethylglycin hydrochloride. This solution was mixed with a solution of 1.0 g of 6-(p-aminophenyl)-5-methyl-4,5-dihydro-3(2H)-pyridazinone in 20 ml of dimethylformamide. To this mixture was added under ice-cooling 1.2 g of dicyclohexylcarbodiimide, and the reaction was effected for 2 hours. The reaction mixture was allowed to stand for 2 days in a cool place and concentrated under reduced pressure. Water was added to the residue and any insoluble matter was eliminated by filtration. Sodium hydrogen carbonate was added to the filtrate to make it alkaline whereby crystals were precipitated which were then recrystallized from methanol-water to obtain 950 mg of the end product. M.P. 195°-197° C.

Workup

  1. additionTo this mixture was added under ice-
  2. waitto stand for 2 days in a cool place
  3. concentrationconcentrated under reduced pressure
  4. additionWater was added to the residue
  5. filtrationany insoluble matter was eliminated by filtration
  6. additionSodium hydrogen carbonate was added to the filtrate
  7. customwere precipitated which
  8. customwere then recrystallized from methanol-water

Sources & evidence

ORD record
ord-58f42b0abfdd47dc980954a8349f0e1e
Source dataset
uspto-grants-1987_01
Patent number
US04639451

Reaction notes

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