Acetonitrile → 1-(2-Methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

HRID 28058

反応式

HRID 28058 の反応式
Cl.[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[NH:9][C:10]([NH:12][C:13](=[NH:16])[NH:14][CH3:15])=[O:11].[CH3:17]C#N.COC(OC)N(C)C.[NH4+].[OH-]>C(Cl)(Cl)Cl.O.CO>[CH3:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[N:9]1[CH:15]=[N:14][C:13]([NH:16][CH3:17])=[N:12][C:10]1=[O:11]

参加物

7

反応物 4

HCID 6342Acetonitrile2 回HCID 14923Ammonium HydroxideHCID 78373Dimethylformamide dimethyl acetalHCID 178485163HCID 178485163、化合物

生成物 1

HCID 130393701-(2-Methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 22418719Chloroform water溶媒

実験手順

To a magnetically stirred suspension of 9.72 g. (40 mmol) of 1-(2'-methylphenyl)-3-methylamidinourea hydrochloride in 30 ml. of CH3CN is added 9.52 g. (80 ml.) of N,N-dimethylformamide dimethylacetal. After the mixture is further diluted with 25 ml. CH3CN and stirred for 5 minutes all of the solid is dissolved. TLC (3% NH4OH) shows a new spot; about equal in size to a spot in starting material; (EtoAc/MeOH; 9:1) shows mostly a new spot. The solution is refluxed for 2 hours. The reaction mixture is allowed to cool to ambient temperature. The reaction mixture is then poured into CHCl3 /H2O and separated. The aqueous layer is extracted with CHCl3 (for a total of 3×50 ml.). The organic layers are combined and washed with H2O (2×50 ml.). The aqueous layers are combined and back extracted with CHCl3 (1×50 ml.). All organic layers are combined, dried, filtered and concentrated in vacuo to yield the product which is recrystallized from absolute EtOH, filtered and washed with cold absolute EtOH and air-dried. The product is 1-(2'-methylphenyl)-4-methylamino-1,2-dihydro-1,3,5-triazin-2-one, melting point 191.5°-192.5° C.

後処理

  1. additionTo a magnetically stirred suspension of 9.72 g
  2. additionAfter the mixture is further diluted with 25 ml
  3. dissolutionis dissolved
  4. temperatureThe solution is refluxed for 2 hours
  5. customseparated
  6. extractionThe aqueous layer is extracted with CHCl3 (for a total of 3×50 ml
  7. washwashed with H2O (2×50 ml.)
  8. extractionback extracted with CHCl3 (1×50 ml.)
  9. customdried
  10. filtrationfiltered
  11. concentrationconcentrated in vacuo
  12. customto yield the product which
  13. customis recrystallized from absolute EtOH
  14. filtrationfiltered
  15. washwashed with cold absolute EtOH
  16. customair-dried

出典と根拠

ORDレコード
ord-c9155fe5000a4ebcba9e15b51d590a1b
出典データセット
uspto-grants-1980_09
特許番号
US04225315

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