Boron trifluoride etherate → HCID 178513156、化合物

HRID 2203327ノート

反応式

HRID 2203327 の反応式
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[C:9](=O)[CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14].[C:20]([NH:23][NH2:24])([NH2:22])=[NH:21].Cl.B(F)(F)F.CCOCC>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1/[C:9](=[N:24]/[NH:23][C:20](=[NH:21])[NH2:22])/[CH2:10][CH2:11][C:12]([F:18])([F:17])[C:13]([F:16])([F:15])[F:14]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 866789671-(2-Bromo-5-chlorophenyl)-4,4,5,5,5-pentafluoropentan-1-oneHCID 178418668HCID 178418668、化合物

生成物 1

HCID 178513156HCID 178513156、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
100 °C

実験手順

To a screw cap pressure vessel was added the intermediate from Step B (0.450 g, 1.2 mmol), aminoguanidine hydrochloride (0.456 g, 6.2 mmol), methanol (20 mL) and boron trifluoride diethyl etherate (0.94 mL, 7.4 mmol). The reaction solution was heated at 100° C. for 3 hours. The solution was concentrated and the residue partitioned between EtOAc and aqueous 1N NaOH. The organic phase was washed twice with aqueous 1N NaOH and brine (1×). The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated to give the indicated compound as a mixture of E,Z hyrazone isomers. 1H NMR (500 MHz, CH3OH-d4): δ 7.60 (d, J=8.6 Hz, 1H); 7.26-7.23 (m, 1H); 7.18 (d, J=2.5 Hz, 1H); 2.74 (s, 2H); 2.56 (s, 2H). m/z=421.2 (M+H).

後処理

  1. customTo a screw cap pressure vessel
  2. concentrationThe solution was concentrated
  3. customthe residue partitioned between EtOAc and aqueous 1N NaOH
  4. washThe organic phase was washed twice with aqueous 1N NaOH and brine (1×)
  5. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the indicated compound
  9. additionas a mixture of E,Z hyrazone isomers

出典と根拠

ORDレコード
ord-04af3ed8111f40aa97bd75802e5ce216
出典データセット
uspto-grants-2016_06
特許番号
US09365574B2

反応ノート

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