Acetohydrazide → 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one

HRID 1485375ノート

反応式

HRID 1485375 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12](=S)[NH:11][C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1.[C:21]([NH:24][NH2:25])(=O)[CH3:22]>C(O)CCC>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:14](=[O:15])[CH2:13][C:12]3=[N:25][N:24]=[C:21]([CH3:22])[N:11]3[C:10]3[CH:17]=[CH:18][CH:19]=[CH:20][C:9]2=3)=[CH:4][CH:3]=1

参加物

4

反応物 2

HCID 14039AcetohydrazideHCID 867184911-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one

生成物 1

HCID 709795286-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one収率 40.1%

試薬・触媒・溶媒 1

HCID 2631-Butanol溶媒

実験手順

A solution of 1-(4-chlorophenyl)-4-thioxo-4,5-dihydro-1H-benzo[b][1,4]diazepin-2(3H)-one (1.0 g, 3.3 mmol) and acetohydrazide (1.23 g, 16.6 mmol) in n-butanol (20 ml) was refluxed for 24 h under N2 atmosphere. The solvent was evaporated in vacuo and partitioned between DCM (100 mL) and water (50 mL). The organic phase was dried over Na2SO4 and the solvent was evaporated in vacuo to afford a residue. The residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1) to give 6-(4-chlorophenyl)-1-methyl-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-5(6H)-one (430.0 mg, 40%). LRMS (M+H+) m/z: calcd 324.08. found 324. 1H NMR (300 MHz, CD3OD): δ 2.72 (s, 3H), 3.94 (q, J=14.1 Hz, 2H), 7.15-7.24 (m, 3H), 7.40-7.52 (m, 4H), 7.70-7.73 (m, 1H).

後処理

  1. customThe solvent was evaporated in vacuo
  2. custompartitioned between DCM (100 mL) and water (50 mL)
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customthe solvent was evaporated in vacuo
  5. customto afford a residue
  6. customThe residue was purified by column chromatography (silica-gel, DCM:MEOH=30:1)

出典と根拠

ORDレコード
ord-ec9d33ff21eb4d0895cb1a342376606d
出典データセット
uspto-grants-2016_08
特許番号
US09422292B2

反応ノート

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