Toluene → HCID 18940674、化合物

HRID 355751ノート

反応式

HRID 355751 の反応式
[CH:1]1([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=O)=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)(Cl)=O.C1(C)C=CC=CC=1.[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH2:35])=[CH:31][C:30]=1[N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1>ClCCl.C(N(CC)CC)C>[CH3:27][O:28][C:29]1[CH:34]=[CH:33][C:32]([NH:35][C:11](=[O:13])[C:10]2[CH:9]=[CH:8][C:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)=[CH:15][CH:14]=2)=[CH:31][C:30]=1[N:36]1[CH2:37][CH2:38][N:39]([CH3:42])[CH2:40][CH2:41]1

参加物

7

反応物 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 883374-Cyclohexylbenzoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

生成物 1

HCID 18940674HCID 18940674、化合物収率 92%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8471Triethylamine溶媒

実験手順

4-Cyclohexylbenzoic acid (300 mg, 1.5 mmol) was heated at reflux with thionyl chloride (2 ml) and toluene (40 ml) for 2 h, and then evaporated to dryness under reduced pressure. 4-Methoxy-3-(4-methyl-1-piperazinyl)phenylamine (325 mg, 1.5 mmol) in dry dichloromethane (40 ml) was added with triethylamine (2 ml) and the mixture stirred for 1 h. The solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml), the organic solution dried (sodium sulphate) and evaporated to dryness under reduced pressure to afford an oil, which was purified by flash column chromatography (silica, chloroform/methanol 5%) to afford the title compound (561 mg, 92%) which was crystallised from methanol/diethyl ether as the oxalate salt m.p. 117°-119° C.

後処理

  1. customevaporated to dryness under reduced pressure
  2. customThe solution was partitioned between dichloromethane (40 ml) and saturated aqueous potassium carbonate (40 ml)
  3. dry with materialthe organic solution dried (sodium sulphate)
  4. customevaporated to dryness under reduced pressure
  5. customto afford an oil, which
  6. customwas purified by flash column chromatography (silica, chloroform/methanol 5%)

出典と根拠

ORDレコード
ord-b49adb1682b84888bb73f304ad919862
出典データセット
uspto-grants-1998_11
特許番号
US05834471

反応ノート

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