Sodium Hydroxide → 3-Chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline

HRID 81701

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HRID 81701 반응식
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]#[N:10])=[C:4]([Cl:11])[C:3]=1[CH3:12].O.[SH-].[Na+].[BH4-].[Na+].[OH-].[Na+].[Cl:20][C:21]1N=C(Cl)[CH:24]=[CH:23][N:22]=1>CO.O>[Cl:11][C:4]1[C:3]([CH3:12])=[C:2]([CH:7]=[CH:6][C:5]=1[S:8][C:9]1[CH:24]=[CH:23][N:22]=[C:21]([Cl:20])[N:10]=1)[NH2:1]

참가 물질

7

반응물 5

HCID 14798Sodium HydroxideHCID 775312,4-DichloropyrimidineHCID 4311764Sodium borohydrideHCID 16211346Sodium hydrosulfide hydrateHCID 378593093-Chloro-2-methyl-4-thiocyanatoaniline

생성물 1

HCID 594916743-Chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline수율 51.4%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

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온도
0 °C

실험 절차

Crude 4-amino-2-chloro-3-methylphenyl thiocyanate (600 mg, 3.0 mmol) was dissolved in a mixture of methanol:water (2:1, 22 mL) and cooled to 0° C. Sodium hydrosulfide monohydrate (338 mg, 4.6 mmol) and sodium borohydride (447 mg, 11.8 mmol) were added then the mixture was allowed to warm to room temperature and stir overnight. After this time sodium hydroxide (96 mg, 2.4 mmol) was added followed by 2,4-dichloropyrimidine (360 mg, 2.4 mmol) and the mixture allowed to stir for a further 24 h. The methanol was removed in vacuo and then the mixture was extracted with ethyl acetate. The extracts were dried (Na2SO4) and evaporated then the residue was purified by flash chromatography to afford 3-chloro-4-[(2-chloropyrimidin-4-yl)thio]-2-methylaniline (353 mg, 41%).

후처리

  1. temperatureto warm to room temperature
  2. stirringto stir for a further 24 h
  3. customThe methanol was removed in vacuo
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe extracts were dried (Na2SO4)
  6. customevaporated
  7. customthe residue was purified by flash chromatography

출처 및 근거

ORD 기록
ord-4ade47deac6c4594a6d8c90bd28d38c0
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846704B2

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