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Cyanuric chloride → 4-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile

HRID 25044
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HRID 25044 반응식
Br[CH2:2][C:3]1[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:10].[Mg].Cl[C:13]1[N:18]=[C:17](Cl)[N:16]=[C:15]([Cl:20])[N:14]=1.[NH2:21][C:22]1[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=1>C(OCC)C.C1C=CC=CC=1.C(N(CC)C(C)C)(C)C.O1CCOCC1>[Cl:20][C:15]1[N:14]=[C:13]([CH2:2][C:3]2[C:8]([Cl:9])=[CH:7][CH:6]=[CH:5][C:4]=2[Cl:10])[N:18]=[C:17]([NH:21][C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[N:16]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

9

반응물 4

HCID 7954Cyanuric chlorideHCID 133964-AminobenzonitrileHCID 301591-Bromomethyl-2,6-dichlorobenzene2회HCID 5462224Magnesium

생성물 1

HCID 4864234-[[4-Chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]amino]benzonitrile수율 104.2%

시약·촉매·용매 4

HCID 241
Benzene
용매
HCID 3283Diethyl Ether용매3회
HCID 312751,4-Dioxane용매
HCID 81531Diisopropylethylamine용매

실험 절차

A solution of 2-(bromomethyl)-1,3-dichlorobenzene (about 10% of 0.383 mol) in diethylether (240 ml) was added to magnesium (0.383 mol) in diethylether (240 ml) under argon. Once the reaction started, the remainder of 2-(bromomethyl)-1,3-dichlorobenzene in diethylether was added. The solution was stirred at RT for 2.5 hours and then added via canula to a solution of 2,4,6-trichloro-1,3,5-triazine (0.319 mol) in benzene (480 ml) while keeping the temperature below 15° C. The reaction mixture was stirred for one hour in an ice bath, then for 2 hours at RT. A solution of 4-amino-benzonitrile (0.351 mol) in N,N-diisopropylethylamine (61.0 ml) and 1,4-dioxane (500 ml) was added and the reaction mixture was stirred at RT for 40 hours. The solvent was evaporated. Water and ethylacetate were added. The solution was stirred, then the solid was filtered off, washed with ethylacetate and water, yielding 129.9 g of 4-[[4-chloro-6-[(2,6-dichlorophenyl)methyl]-1,3,5-triazin-2-yl]-amino]benzonitrile (intermediate 27; mp. 243-244° C.).

후처리

  1. customthe temperature below 15° C
  2. stirringThe reaction mixture was stirred for one hour in an ice bath
  3. waitfor 2 hours at RT
  4. stirringthe reaction mixture was stirred at RT for 40 hours
  5. customThe solvent was evaporated
  6. additionWater and ethylacetate were added
  7. stirringThe solution was stirred
  8. filtrationthe solid was filtered off
  9. washwashed with ethylacetate and water

출처 및 근거

ORD 기록
ord-a24fe50e94d9483d807f5b9ce3c92b2c
출처 데이터셋
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06858609B2

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