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

HRID 126759
ノート
印刷プレビュー

反応式

HRID 126759 の反応式
[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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒
HCID 6344
Dichloromethane
溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-4de95c22b07d4c588c9b466cc74a1852
出典データセット
uspto-grants-1981_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04254122

反応ノート

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