Hydrochloric Acid → 6-Diphenylphosphorylamino nicotinamide

HRID 127944Notes

Reaction equation

HRID 127944 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=1.N1C=CC=CC=1.[C:17]1([P:23](Cl)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.Cl>N1CCCC1=O.C(O)C.C(Cl)(Cl)Cl>[C:17]1([P:23]([NH:1][C:2]2[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][N:3]=2)([C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:24])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 1049PyridineHCID 95006-AminonicotinamideHCID 73910Diphenylphosphinic chloride

Product 1

HCID 234709116-Diphenylphosphorylamino nicotinamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 6212ChloroformSolventHCID 120252-PyrrolidoneSolvent

Procedure

6-Aminonicotinamide 1.37 g (0.01 mole) is dissolved in 10 ml of 2-pyrrolidinone and 3 ml of pyridine by gentle warming of the mixture. Diphenylphosphoryl chloride 6 ml (0.024 mole) is then slowly added to the mixture. After 1 hour of reaction at room temperature, the mixture is poured into 300 ml of 0.2 N HCl. A reddish syrup, 2.2 g which is formed in the bottom of the flask is isolated by decantation. The product may be purified as follows. The reddish syrup obtained above is dissolved in 3 ml of ethanol and the solution is admixed with 200 ml of 0.2 N HCl. Chloroform, 100 ml is added to the mixture to extract the product. After dried over anhydrous sodium sulfate the chloroform solution which contains the product is evaporated at 35° C. in vacuum to give a practically pure 6-diphenylphosphorylamino nicotinamide.

Workup

  1. customAfter 1 hour of reaction at room temperature
  2. customA reddish syrup, 2.2 g which is formed in the bottom of the flask
  3. customis isolated by decantation
  4. customThe product may be purified
  5. customThe reddish syrup obtained
  6. extractionto extract the product
  7. dry with materialAfter dried over anhydrous sodium sulfate the chloroform solution which
  8. customis evaporated at 35° C. in vacuum

Sources & evidence

ORD record
ord-1d85b24c53974f18bd577b30b6e9f217
Source dataset
uspto-grants-1981_03
Patent number
US04258052

Reaction notes

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