Toluene → 3-(9-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2,4-difluorophenyl)-4H-1,2,4-triazole

HRID 1949840ノート

反応式

HRID 1949840 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([C:15]([NH2:17])=O)[S:8][C:7]=3[C:6]=2[CH:18]=1.CO[CH:21](OC)[N:22](C)C.C1(C)C=CC=CC=1.Cl.[F:35][C:36]1[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:37]=1[NH:43]N>C(O)(=O)C.ClCCl.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[CH:10]=[C:9]([C:15]4[N:43]([C:37]5[CH:38]=[CH:39][C:40]([F:42])=[CH:41][C:36]=5[F:35])[CH:21]=[N:22][N:17]=4)[S:8][C:7]=3[C:6]=2[CH:18]=1

参加物

8

反応物 4

HCID 1140TolueneHCID 78373Dimethylformamide dimethyl acetalHCID 27333012,4-Difluorophenylhydrazine hydrochlorideHCID 668685379-Bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid amide

生成物 1

HCID 579003503-(9-bromo-4,5-dihydrobenzo[b]thieno[2,3-d]oxepin-2-yl)-4-(2,4-difluorophenyl)-4H-1,2,4-triazole

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
100 °C

実験手順

A mixture of 9-bromo-4,5-dihydro-6-oxa-1-thia-benzo[e]azulene-2-carboxylic acid amide (340 mg), dimethylformamide dimethyl acetal (3 ml) and toluene (2.5 mL) was heated to 100° C. for 16 hours. The solvent was then reduced in vacuo and dissolved in acetic acid (3 ml) and water (0.3 mL) and to this was added 2,4-difluorophenylhydrazine hydrochloride (265 mg). The reaction mixture was heated to 100° C. for 3 hours. The reaction mixture was then cooled, and then diluted with dichloromethane, washed with sodium carbonate solution, dried (MgSO4) and the solvent removed in vacuo. Purification using flash chromatography yielded 293. NMR: (CDCl3): 3.15 (2H, t), 4.31 (2H, t), 6.82 (1H, d), 6.86 (1H, s), 7.08-7.13 (2H, m), one proton under chloroform peak, 7.72 (1H, s), 8.10 (1H, s)

後処理

  1. temperatureThe reaction mixture was heated to 100° C. for 3 hours
  2. temperatureThe reaction mixture was then cooled
  3. washwashed with sodium carbonate solution
  4. dry with materialdried (MgSO4)
  5. customthe solvent removed in vacuo
  6. customPurification

出典と根拠

ORDレコード
ord-d9e78001157f4f338faa0e06d2e450cb
出典データセット
uspto-grants-2013_03
特許番号
US08399690B2

反応ノート

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