Alloxan → 5-(2-chloro-3-thienyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

HRID 1262941Notes

Reaction equation

HRID 1262941 reaction equation
[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1Br.C([Li])CCC.[NH:13]1[C:21](=[O:22])[C:19](=O)[C:17](=[O:18])[NH:16][C:14]1=[O:15]>CCOCC.O1CCCC1>[Cl:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH:19]1[C:17](=[O:18])[NH:16][C:14](=[O:15])[NH:13][C:21]1=[O:22]

Participants

6

Reactant 3

HCID 5781AlloxanHCID 27245593-Bromo-2-chlorothiopheneHCID 178418339Butyllithium

Product 1

HCID 204564725-(2-chloro-3-thienyl)-2,4,6(1H,3H,5H)-pyrimidinetrione

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following the method of Gronowitz et al. [Chemica Scripta 15, p. 2 (1980)], 2-chloro-3-bromothiophene is reacted with n-butyl lithium in ether at -70° C. After 15 minutes, the organolithium reagent is poured into a solution of alloxan in tetrahydrofuran at -70° C. The reaction mixture is allowed to warm to room temperature for 2 hours, and 5-(2-chloro-3-thienyl)-2,4,6(1H,3H,5H)-pyrimidinetrione isolated according to Example 5.

Sources & evidence

ORD record
ord-57e9456397fa4d888db3ca43187e73b4
Source dataset
uspto-grants-1984_06
Patent number
US04454320

Reaction notes

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