Malonic Acid → 1-(2-isocyanobenzyl)-3-methylpyrimidine-2,4,6(1H,3H,5H)-trione

HRID 78685Notes

Reaction equation

[N+:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[CH2:5][NH:6][C:7]([NH:9][CH3:10])=[O:8])#[C-:2].[C:15]([OH:21])(=O)[CH2:16][C:17]([OH:19])=O.C(OC(=O)C)(=O)C>C(O)(=O)C>[N+:1]([C:3]1[CH:14]=[CH:13][CH:12]=[CH:11][C:4]=1[CH2:5][N:6]1[C:15](=[O:21])[CH2:16][C:17](=[O:19])[N:9]([CH3:10])[C:7]1=[O:8])#[C-:2]

Participants

Conditions

Temperature: 60 °C

Procedure

In an alternate embodiment, 1-(2-isocyanobenzyl)-3-methylurea (30 g), acetic acid (105 ml) and malonic acid (18 g) were mixed and heated to 60° C. Acetic anhydride (60 ml) was added at 60° C. and heating was continued for two hours at 80° C. The reaction mixture was poured over ice water (300 ml) and the obtained solid was filtered, washed with water (1×500 ml) and methyl-tert-butylether (100 ml). The yield is 60% with 93.4% purity.

Workup

temperatureheating
filtrationthe obtained solid was filtered
washwashed with water (1×500 ml) and methyl-tert-butylether (100 ml)

Sources & evidence

ORD record: ord-44d12978075e429d9d3d11553150a671
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08841447B2

Reaction notes

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