Triethylamine → 2-(N',N'-diethylcarbamoyl)ethyl isocyanate

HRID 1702778Notes

Reaction equation

HRID 1702778 reaction equation
[CH2:1]([N:3]([CH2:11][CH3:12])[C:4]([CH2:6][CH2:7]C(O)=O)=[O:5])[CH3:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C>C1C=CC=CC=1>[CH2:11]([N:3]([CH2:1][CH3:2])[C:4]([CH2:6][CH2:7][N:32]=[C:35]=[O:20])=[O:5])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15205Butanoic acid, 4-(diethylamino)-4-oxo- (9CI)HCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 205250482-(N',N'-diethylcarbamoyl)ethyl isocyanate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

The reaction of 3-(N,N-diethylcarbamoyl)propionic acid and diphenylphosphoryl azide in a solution of triethylamine and benzene provided a solution comprising 2-(N',N'-diethylcarbamoyl)ethyl isocyanate (I.R.: 2290 cm-1), which was reacted with 5-fluorouracil to provide 1-[N-[2-(N',N'-diethylcarbamoyl)ethyl]carbamoyl]-5-fluorouracil substantially in the similar method to that of Example 4.

Sources & evidence

ORD record
ord-e3ea8f59aac94313a99d07ca2aee7126
Source dataset
uspto-grants-1982_09
Patent number
US04349552

Reaction notes

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