4-(Bromoacetyl)benzonitrile → 4-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1992560ノート

反応式

HRID 1992560 の反応式
[OH:1][CH2:2][C:3]([NH:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][CH:13]=2)[N:11]=1)([CH3:5])[CH3:4].BrCC(C1C=CC([C:28]#[N:29])=CC=1)=O.C1N=CN(C(N2C=NC=C2)=N)C=1>O1CCCC1>[NH:29]=[C:28]1[N:6]([C:7]2[S:8][CH:9]=[C:10]([C:12]3[CH:13]=[CH:14][C:15]([C:16]#[N:17])=[CH:18][CH:19]=3)[N:11]=2)[C:3]([CH3:5])([CH3:4])[CH2:2][O:1]1

参加物

5

反応物 3

HCID 986544-(Bromoacetyl)benzonitrileHCID 113556541-(1H-imidazole-1-carboximidoyl)-1H-imidazoleHCID 866185984-{2-[(2-Hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile

生成物 1

HCID 247845394-[2-(2-Imino-4,4-dimethyl-1,3-oxazolidin-3-yl)-1,3-thiazol-4-yl]benzonitrile収率 19%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 4-{2-[(2-hydroxy-1,1-dimethylethyl)amino]-1,3-thiazol-4-yl}benzonitrile (2.00 g, 7.31 mmol), prepared in the same manner as described in step 3 of Example 3, and replacing 3-(2-bromoacetyl)benzonitrile with 4-(2-bromoacetyl)benzonitrile, and C-(di-imidazol-1-yl)-methyleneamine (1.30 g, 8.07 mmol) in 35 mL of tetrahydrofuran was refluxed under nitrogen for three days. The reaction was concentrated under reduced pressure to remove the tetrahydrofuran. The residue was partitioned between methylene chloride and water. The organic layer was separated, dried (MgSO4), filtered and the solvent removed under reduced pressure. Purification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge) using a linear gradient of hexane in methylene chloride as the eluent gave the title compound (417.2 mg, 19%) as an off-white solid, mp 158-161° C.; MS (ES) m/z 299.0 [M+H]+. Anal. Calcd for C15H14N4OS: C, 60.38; H, 4.73; N, 18.78. Found: C, 60.38; H, 4.82; N, 18.67.

後処理

  1. customprepared in the same manner
  2. temperaturewas refluxed under nitrogen for three days
  3. concentrationThe reaction was concentrated under reduced pressure
  4. customto remove the tetrahydrofuran
  5. customThe residue was partitioned between methylene chloride and water
  6. customThe organic layer was separated
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. customthe solvent removed under reduced pressure
  10. customPurification of the residue on a Horizon™ Flash Collector (the Biotage FLASH 40+™ cartridge)

出典と根拠

ORDレコード
ord-527fcb89c9b34727aa73d307885702fd
出典データセット
uspto-grants-2010_01
特許番号
US07649007B2

反応ノート

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