Acetonitrile → 1-(2',6'-Dichlorophenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one
Reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[NH:10][C:11]([NH:13][C:14](=[NH:17])[NH:15][CH3:16])=[O:12].[CH3:18]C#N.COC(OC)N(C)C>C(NC(N)=O)(=N)N>[Cl:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([Cl:9])[C:4]=1[N:10]1[CH:16]=[N:15][C:14]([NH:17][CH3:18])=[N:13][C:11]1=[O:12]Participants
Procedure
To a magnetically stirred suspension of 11.88 g. (40 mmol) of 1-(2',6'-dichlorophenyl)-3-methylamidinourea hydrochloride in 30 ml. of CH3CN is added 9.52 g. (80 mmol) of N,N-dimethylformamide dimethylacetal in 20 ml. of CH3CN. The solid material begins to dissolve immediately but in a few minutes, before the starting material amidinourea has dissolved, another fine particle white solid begins to precipitate out. The reaction mixture is stirred at ambient temperature for 1 hour then heated to reflux for 2 hours. After 2 hours the reaction mixture is allowed to come to ambient temperature and the white solid precipitate filtered out to yield the desired product, melting point 270° C.; TLC (EtoAc 9:1); one major spot, one minor spot at origin. A small sample recrystallized from CH3OH/EtoAc gave 1 spot on TLC. (9.6 g. 89%). The product is recrystallized from MeOH to yield 1-(2',6'-dichlorophenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one.
Workup
- additionTo a magnetically stirred suspension of 11.88 g
- dissolutionhas dissolved
- customto precipitate out
- temperaturethen heated
- temperatureto reflux for 2 hours
- waitAfter 2 hours the reaction mixture is allowed
- customto come to ambient temperature
- filtrationthe white solid precipitate filtered out
Sources & evidence
- ORD record
- ord-bea7673b1315495ea1602dd13c470e57
- Source dataset
- uspto-grants-1982_07
- Patent number
- US04338441
Reaction notes
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