Cl[C:2]1[N:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[N:4][C:3]=1Cl.[CH2:11]([NH:15][CH:16](O)[CH3:17])[CH2:12][CH2:13][CH3:14].C(=O)([O-])[O-:20].[K+].[K+].[OH-].[K+]>O1CCOCC1.O>[CH2:11]([N:15]1[CH2:16][CH2:17][O:20][C:3]2[N:4]=[C:5]([Cl:9])[C:6]([Cl:8])=[N:7][C:2]1=2)[CH2:12][CH2:13][CH3:14]
A mixture of tetrachloropyrazine (21.8 g, 0.1 mol), n-butylaminoethanol (11.7 g, 0.1 mol), and potassium carbonate (28 g, 0.2 mol) were heated to 80° in 225 ml of dioxane and 50 ml of water for 24 hours. After extraction with CH2Cl2 and concentration with rotary evaporation, 30 g of an oil characterized by nmr as the N-substituted product was obtained. An attempt to distill 5 g of this material led to decomposition. The rest of the material was dissolved in 200 ml of benzene and refluxed for 2 hours with crushed KOH (10 g, 85% assay, 0.15 mol). The mixture was partitioned between water and CH2Cl2. The organic layer was dried (MgSO4) and rotary evaporated to give a crude oil. This was distilled two times on a Kugelrohr apparatus (b.p. about 130° at 0.5 mm Hg) to give 12.5 g (48% yield) of the title product.
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