Alloxan → 5-Hydroxy-5-(2-benzthiazolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

HRID 1285154Notes

Reaction equation

[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[NH:10]1[C:18](=[O:19])[C:16](=[O:17])[C:14](=[O:15])[NH:13][C:11]1=[O:12]>>[OH:17][C:16]1([C:2]2[S:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[N:3]=2)[C:14](=[O:15])[NH:13][C:11](=[O:12])[NH:10][C:18]1=[O:19]

Participants

Reactant 2

HCID 5781Alloxan

HCID 7222Benzothiazole

Product 1

HCID 212712615-Hydroxy-5-(2-benzthiazolyl)-2,4,6-(1H,3H,5H)pyrimidinetrione

Procedure

By the procedure of Example 38, benzthiazole (2.7 g., 0.02 moles) was converted to its 2-lithio derivative and then reacted with anhydrous alloxan to yield title product, initially isolated as an oil. The latter was crystallized from ether-hexane [2.2 g.; Rf 0.55 (1:1 ethyl acetate:hexane/5% acetic acid)].

Sources & evidence

ORD record: ord-7bc09822cafc4400ae9c77ef35da225d
Source dataset: uspto-grants-1986_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04565820

Reaction notes

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