Triethylamine → N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamide

HRID 257854ノート

反応式

HRID 257854 の反応式
[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([S:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH2:12])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:24][N:25]1[C:29]([C:30](Cl)=[O:31])=[C:28]2[CH:33]=[C:34]([CH3:36])[CH:35]=[C:27]2[NH:26]1>C1(C)C=CC=CC=1>[CH3:1][C:2]1[CH:16]=[CH:15][C:5]([S:6][C:7]2[CH:14]=[CH:13][C:10]([CH2:11][NH:12][C:30]([C:29]3[N:25]([CH3:24])[NH:26][C:27]4=[CH:35][C:34]([CH3:36])=[CH:33][C:28]=34)=[O:31])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 435288314-(4-Methylthiophenoxy)benzylamineHCID 867473882,5-Dimethylcyclopenta[1,2-c]-pyrazole-3-carbonyl chloride

生成物 1

HCID 131718252N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamide収率 69.7%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To a stirred mixture of 4-(4-methylthiophenoxy)benzylamine (124 mg, 0.505 mM), triethylamine (61 mg, 0.60 mM) and toluene (20 ml) was added dropwise a solution (10 ml) of 2,5-dimethylcyclopenta[1,2-c]-pyrazole-3-carbonyl chloride(100 mg, 0.503 mM) in toluene at 0°-10° C., and the mixture was stirred for 3 h at the room temperature. The mixture was poured into ice water, and the mixture was extracted with toluene. The extract was washed with saturated sodium hydrogen carbonate solution, water, saturated ammonium chloride solution and brine, dried with magnesium sulfate, and concentrated in vacuo. The residue was chromatographed over silica gel to give N-[4-(4-methylthiophenoxy)benzyl]-2,5-dimethylcyclopenta[1,2-c]pyrazole-3-carboxamide (138 mg, 67%) as colorless crystals, m.p. 138.0° C.

後処理

  1. extractionthe mixture was extracted with toluene
  2. washThe extract was washed with saturated sodium hydrogen carbonate solution, water, saturated ammonium chloride solution and brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was chromatographed over silica gel

出典と根拠

ORDレコード
ord-8cd50ba80a504b4ab884f6bbdee456f1
出典データセット
uspto-grants-1993_11
特許番号
US05264448

反応ノート

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