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

HRID 25044
ノート
印刷プレビュー

反応式

HRID 25044 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 7954Cyanuric chlorideHCID 133964-AminobenzonitrileHCID 301591-Bromomethyl-2,6-dichlorobenzene2 回HCID 5462224Magnesium

生成物 1

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

試薬・触媒・溶媒 4

HCID 241
Benzene
溶媒
HCID 3283Diethyl Ether溶媒3 回
HCID 312751,4-Dioxane溶媒
HCID 81531Diisopropylethylamine溶媒

実験手順

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.).

後処理

  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

出典と根拠

ORDレコード
ord-a24fe50e94d9483d807f5b9ce3c92b2c
出典データセット
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06858609B2

反応ノート

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