Cyanamide → HCID 21357925、化合物

HRID 1167832

反応式

HRID 1167832 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:13]=[C:14]=[S:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[N:16]#[C:17][NH2:18].O(C(C)(C)C)[K].Cl.Cl[CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([Li])CCC>C(#N)C.C(O)(C)(C)C.O.C1COCC1>[N:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[C:27]1[S:15][C:14]([NH:13][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)=[N:16][C:17]=1[NH2:18]

参加物

9

反応物 5

HCID 9864CyanamideHCID 23392Picolyl chloride hydrochlorideHCID 1189003,4,5-Trimethoxyphenyl isothiocyanateHCID 178418339ButyllithiumHCID 178418922HCID 178418922、化合物

生成物 1

HCID 21357925HCID 21357925、化合物

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 22050040Acetonitrile tert-butanol溶媒

反応条件

温度
23 °C

実験手順

3,4,5-Trimethoxyphenyl isothiocynate (250 mg, 1.11 mmol, 1 equiv.) and cyanamide (56 mg, 1.33 mmol, 1.2 equiv.) were taken up in acetonitrile-tert-butanol (1:1, 10 mL) at 23° C. To this was added KO-t-Bu (286 mg, 2.55 mmol, 2.3 equiv.) and 2-chloromethylpyridine hydrochloride (182 mg, 1.11 mmol, 1.00 equiv.). The reaction mixture was allowed to stir for 1.5 h at 23° C. The mixture was diluted with water (20 mL) and the white solids were filtered, washed with ether and dried (257 mg). The dried residue (60 mg, 0.167 mmol, 1.00 equiv.) was dissolved in THF (3 mL), cooled to −78° C. and was treated with n-butyllithium (0.261 mL, 1.6 M, 2.5 equiv.). The mixture was allowed to warm to 23° C., was quenched with saturated sodium bicarbonate, and organics were extracted into ethyl acetate. The concentrated residue was purified by silica gel chromatography (ethyl acetate/hexane: 1:1, 48.3 mg, 80%).

後処理

  1. filtrationthe white solids were filtered
  2. washwashed with ether
  3. customdried (257 mg)
  4. temperaturecooled to −78° C.
  5. temperatureto warm to 23° C.
  6. customwas quenched with saturated sodium bicarbonate
  7. extractionorganics were extracted into ethyl acetate
  8. customThe concentrated residue was purified by silica gel chromatography (ethyl acetate/hexane: 1:1, 48.3 mg, 80%)

出典と根拠

ORDレコード
ord-2cfece655d2e4757a83b8b57afa54f42
出典データセット
uspto-grants-2003_09
特許番号
US06620828B2

関連ノート

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