Triethylamine → HCID 44212503、化合物

HRID 355740ノート

反応式

HRID 355740 の反応式
[N:1]1([C:6]2[CH:14]=[CH:13][C:9]([C:10]([OH:12])=O)=[CH:8][CH:7]=2)[CH:5]=[N:4][CH:3]=[N:2]1.S(Cl)(Cl)=O.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][C:22]=1[N:28]1[CH2:33][CH2:32][N:31]([CH3:34])[CH2:30][CH2:29]1.C(N(CC)CC)C>C1(C)C=CC=CC=1>[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([NH:27][C:10](=[O:12])[C:9]2[CH:8]=[CH:7][C:6]([N:1]3[CH:5]=[N:4][CH:3]=[N:2]3)=[CH:14][CH:13]=2)=[CH:23][C:22]=1[N:28]1[CH2:29][CH2:30][N:31]([CH3:34])[CH2:32][CH2:33]1

参加物

6

反応物 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 7365314-(1H-1,2,4-Triazol-1-yl)benzoic acidHCID 103311014-Methoxy-3-(4-methylpiperazin-1-yl)aniline

生成物 1

HCID 44212503HCID 44212503、化合物収率 92%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Ethyl 4-(1,2,4-triazol-1-yl)benzoate (520 mg, 2.4 mmol) was heated at reflux in 5N HCl (40 ml) for 1 h, and the product filtered off and dried in vacuo to afford the acid (88%). 4-(1,2,4triazol-1-yl)benzoic acid (0.395 g, 2.1 mmol) was suspended in dry toluene (40 ml) and thionyl chloride (2 ml) added under argon. The mixture was heated to reflux for 1.5 h and then evaporated to dryness under reduced pressure. The oil was dissolved in dichloromethane under argon and 4-methoxy-3-(4-methyl-1-piperazinyl)phenylamine (460 mg, 2.1 mmol) was added followed by triethylamine (2 ml). The mixture was stirred at room temperature under argon for 2 h and then partitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml), and the organic extracts dried (sodium sulphate). The organic solution was filtered, evaporated to dryness under reduced pressure and purified by column chromatography (silica, chloroform/methanol 5-10%) to afford the amide (757 mg, 92%) which was crystallised from methanol diethyl ether as the oxalate salt.

後処理

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1.5 h
  3. customevaporated to dryness under reduced pressure
  4. dissolutionThe oil was dissolved in dichloromethane under argon
  5. custompartitioned between dichloromethane (50 ml) and saturated potassium carbonate (50 ml)
  6. dry with materialthe organic extracts dried (sodium sulphate)
  7. filtrationThe organic solution was filtered
  8. customevaporated to dryness under reduced pressure
  9. custompurified by column chromatography (silica, chloroform/methanol 5-10%)

出典と根拠

ORDレコード
ord-1e01bc38112a42efaaea04ddc23ffefe
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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