Cyanamide → HCID 21357925, 화합물

HRID 1167832

반응식

HRID 1167832 반응식
[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]

참가 물질

9

반응물 5

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

생성물 1

HCID 21357925HCID 21357925, 화합물

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 22050040Acetonitrile tert-butanol용매

반응 조건

온도
23 °C

실험 절차

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%).

후처리

  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%)

출처 및 근거

ORD 기록
ord-2cfece655d2e4757a83b8b57afa54f42
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06620828B2

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