3-(Trifluoromethyl)phenyl isocyanate → 3-(3-Trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione

HRID 126759

반응식

HRID 126759 반응식
[NH2:1][C:2](=[N:5][C:6](=[O:9])OC)[S:3][CH3:4].[F:10][C:11]([F:22])([F:21])[C:12]1[CH:13]=[C:14]([N:18]=[C:19]=[O:20])[CH:15]=[CH:16][CH:17]=1.[Na]>C(Cl)Cl.CO>[F:10][C:11]([F:21])([F:22])[C:12]1[CH:13]=[C:14]([N:18]2[C:19](=[O:20])[NH:1][CH:2]([S:3][CH3:4])[NH:5][C:6]2=[O:9])[CH:15]=[CH:16][CH:17]=1

참가 물질

6

반응물 3

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 2935781-methoxycarbonyl-S-methylisothioureaHCID 5360545Sodium

생성물 1

HCID 705459153-(3-Trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione수율 86%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Methyl N-[1-(amino)-1-(methylthio)methylene]carbamate (14.8 g.) was dissolved in methylene chloride (150 ml.). 3-Trifluoromethylphenyl isocyanate (18.7 g.) was added to the solution during 5 minutes and the mixture was stirred at room temperature for 2.5 hours. A freshly prepared solution of sodium (2.3 g.) in methanol (20 ml.) was then added during 5 minutes and the subsequent mixture was stirred at room temperature for 16 hours. The mixture was then evaporated and the residue was dissolved in water (400 ml.). The aqueous solution obtained, was extracted with ethyl acetate (2×400 ml.) to remove neutral byproducts, and then acidified with concentrated hydrochloric acid to pH1. The solid which precipitated was separated by filtration, washed with water (3×500 ml.), and dried (over phosphorus pentoxide) to give 3-(3-trifluoromethylphenyl)-6-methylthio-tetrahydro-1,3,5-triazine-2,4-dione (25.9 g., 86%) as a white solid, m.p. 225°-228° C.

후처리

  1. stirringthe subsequent mixture was stirred at room temperature for 16 hours
  2. customThe mixture was then evaporated
  3. dissolutionthe residue was dissolved in water (400 ml.)
  4. customThe aqueous solution obtained
  5. extractionwas extracted with ethyl acetate (2×400 ml.)
  6. customto remove neutral byproducts
  7. customThe solid which precipitated
  8. customwas separated by filtration
  9. washwashed with water (3×500 ml.)
  10. dry with materialdried (over phosphorus pentoxide)

출처 및 근거

ORD 기록
ord-4de95c22b07d4c588c9b466cc74a1852
출처 데이터셋
uspto-grants-1981_03
특허 번호
US04254122

연결된 노트

불러오는 중…