CC1C=CC=C(C)C=1NC(NC(=N)NOC)=[O:11].CN(C(OC)OC)C.[NH4+].[OH-].[CH3:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH3:35])[C:30]=1[N:36]1[CH:41]=[N:40][C:39]([NH:42][O:43][CH3:44])=[N:38][C:37]1=[O:45]>CC#N.CCOCC.CN(C=O)C>[OH2:11].[CH3:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:29]([CH3:28])[C:30]=1[N:36]1[CH:41]=[N:40][C:39]([NH:42][O:43][CH3:44])=[N:38][C:37]1=[O:45]To a suspension of 10.9 g. (40.0 mmol) of 1-(2',6'-dimethylphenyl)-3-methoxyamidinourea in CH3CN (50 ml.) is added 9.5 g. (80.0 mmol) of DMF-DMA and the mixture heated at 105°-110° C. in a closed bomb for 1-1/2 hours. The reaction mixture is cooled and poured into a round bottom flask and the CH3CN removed under reduced pressure. The residue is partitioned between CHCl3 and H2O and the layer separated. The aqueous layer is extracted with CHCl3 (1×75 ml.). The combined organic layers are washed with H2O (1×50 ml.), dried (MgSO4) and concentrated under reduced pressure to give an oily residue. The residue is taken up in Et2O and washed with H2O (2×50 ml.). The Et2O layer is dried (MgSO4) and concentrated under reduced pressure to give a viscous oil. NMR shows that DMF has been removed. The oil is taken up in hot CH3CN cooled and a small amount of CHCl3, H2O and DMSO insoluble material filtered off. The filtrate is concentrated to give a viscous oil. TLC of the oil (Silicagel; 3% NH4OH, iPA) versus starting material shows one spot moves slower than starting material. Upon addition of MEOH and warming on a steam bath the oil solidifies. The solid is crystallized from MeOH to give 4.6 g. (43%) of 1-(2',6'-dimethylphenyl)-4-methoxyamino-1,2-dihydro-1,3,5-triazin-2-one as a white solid, melting point 78°-80° C.
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