Triethylamine → N-ethyl-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

HRID 1632904ノート

反応式

HRID 1632904 の反応式
[CH2:1]([NH:3][CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1)[CH3:2].[CH2:10]([N:12](CC)CC)[CH3:11].[N+:17]([C:20]1[CH:31]=[CH:30][C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])=[CH:28][C:21]=1[O:22][CH:23]([CH3:27])[C:24](Cl)=[O:25])([O-:19])=[O:18]>C1(C)C=CC=CC=1.C(OCC)(=O)C.CCCCCC>[CH2:1]([N:3]([CH2:4][CH:5]1[O:9][CH2:8][CH2:7][O:6]1)[C:24](=[O:25])[CH:23]([O:22][C:21]1[CH:28]=[C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])[CH:30]=[CH:31][C:20]=1[N+:17]([O-:19])=[O:18])[CH3:27])[CH3:2].[CH2:10]([NH:12][C:24](=[O:25])[C:23]([CH2:4][CH:5]1[O:6][CH2:7][CH2:8][O:9]1)([O:22][C:21]1[CH:28]=[C:29]([O:32][C:33]2[CH:38]=[CH:37][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:35][C:34]=2[Cl:43])[CH:30]=[CH:31][C:20]=1[N+:17]([O-:19])=[O:18])[CH3:27])[CH3:11]

参加物

8

反応物 3

HCID 8471TriethylamineHCID 131006842-[2-Nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl ChlorideHCID 13193169N-(1,3-dioxolan-2-yl)methyl ethylamine

生成物 2

HCID 20441161N-ethyl-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamideHCID 20441181N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide

試薬・触媒・溶媒 3

HCID 1140Toluene溶媒2 回HCID 8058Hexane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

N-Ethyl-N-(1,3-dioxolan-2-ylmethyl)amine (1.31 grams; 0.01 mole), toluene (40 ml) and triethylamine (3 ml) were charged into a glass reaction vessel equipped with a magnetic stirrer, thermometer and addition funnel. A solution of 2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionyl chloride (4.2 grams; 0.01 mole) in toluene (30 ml) was added dropwise, with stirring at room temperature. A slight exotherm was observed. After the addition was completed stirring was continued for a period of about 1.5 hours. After this time the reaction mixture was transferred into a separatory funnel and was washed twice with water (60 ml), with dilute aqueous sodium bicarbonate (60 ml; 5% conc.) and again with water (60 ml). The washed organic phase was dried by passing it through phase separation paper and was thereafter stripped of solvent leaving a viscous oil as the residue. This residue was subjected to chromatography using a clay column (150 ml) and mixtures of ethyl acetate and hexane with increasing concentrations of ethyl acetate as the eluant. Nine fractions were collected. Fractions six and seven were combined and stripped of solvents to yield the desired product N-ethyl-(1,3-dioxolan-2-yl-methyl)-2-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenoxy]propionamide as an amber gum.

後処理

  1. customequipped with a magnetic stirrer
  2. additionthermometer and addition funnel
  3. additionAfter the addition
  4. stirringwas completed stirring
  5. customAfter this time the reaction mixture was transferred into a separatory funnel
  6. washwas washed twice with water (60 ml), with dilute aqueous sodium bicarbonate (60 ml; 5% conc.) and again with water (60 ml)
  7. customThe washed organic phase was dried
  8. customthrough phase separation paper
  9. customleaving a viscous oil as the residue
  10. customNine fractions were collected

出典と根拠

ORDレコード
ord-0549bea5db6745f78d572c9cef199c30
出典データセット
uspto-grants-1984_10
特許番号
US04478634

反応ノート

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