Phosgene → 1,3-Dibutyl-1,3,5-triazinane-2,4,6-trione

HRID 2083436Notes

Reaction equation

HRID 2083436 reaction equation
[C:1](Cl)(Cl)=[O:2].[CH2:5]([NH:9][C:10]([NH:12][CH2:13][CH2:14][CH2:15][CH3:16])=[O:11])[CH2:6][CH2:7][CH3:8].[O-:17][C:18]#[N:19].[K+]>C1C=CC=CC=1>[CH2:13]([N:12]1[C:18](=[O:17])[NH:19][C:1](=[O:2])[N:9]([CH2:5][CH2:6][CH2:7][CH3:8])[C:10]1=[O:11])[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 74523DibutylureaHCID 11378442Potassium cyanate

Product 1

HCID 218207871,3-Dibutyl-1,3,5-triazinane-2,4,6-trioneYield 38%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A benzene solution (50 ml) of 5,3-dibutyl allophanoyl chloride (0.1 mole) was prepared by reaction of phosgene with 1,3-dibutyl urea by the method of Example 2. This material was reacted with 16.0 g (0.2 mole) of potassium cyanate as described above. After work-up, 9.3 g (38% yield) of dibutyl isocyanuric acid was obtained; m.p. 86°-88° C. IR and nmr analysis was consistent with the assigned structure.

Sources & evidence

ORD record
ord-41f14472460441a7a7dddddd6240d4bf
Source dataset
uspto-grants-1978_04
Patent number
US04085268

Reaction notes

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