Triethylamine → 3-isocyanato-N,N-dipropylpropanamide

HRID 1702779Notes

Reaction equation

HRID 1702779 reaction equation
[CH2:1]([N:4]([CH2:12][CH2:13][CH3:14])[C:5]([CH2:7][CH2:8]C(O)=O)=[O:6])[CH2:2][CH3:3].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:34]([CH2:37]C)CC)C>C1C=CC=CC=1>[CH2:12]([N:4]([CH2:1][CH2:2][CH3:3])[C:5]([CH2:7][CH2:8][N:34]=[C:37]=[O:22])=[O:6])[CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 167723133-(Dipropylcarbamoyl)propanoic acid

Product 1

HCID 205250603-isocyanato-N,N-dipropylpropanamide

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The reaction of 3-(N,N-dipropylcarbamoyl)propionic acid and diphenylphosphoryl azide in a solution of triethylamine and benzene provided a solution comprising 2-(N',N'-dipropylcarbamoyl)ethyl isocyanate (I.R.: 2280 cm-1), which was reacted with 5-fluorouracil to provide 1-[N-[2-(N',N'-dipropylcarbamoyl)ethyl]carbamoyl]-5-fluorouracil substantially in the similar method to that of Example 4.

Sources & evidence

ORD record
ord-59938204a81544e5824d608441571880
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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