Sodium Hydroxide → 3,5-Dichloro-4-cyanobenzamide

HRID 1464316

반응식

HRID 1464316 반응식
[C:1]([C:3]1[C:11]([Cl:12])=[CH:10][C:6]([C:7](Cl)=[O:8])=[CH:5][C:4]=1[Cl:13])#[N:2].Cl.[NH2:15]C(C)(CC)C#C.[OH-].[Na+]>O>[C:1]([C:3]1[C:11]([Cl:12])=[CH:10][C:6]([C:7]([NH2:15])=[O:8])=[CH:5][C:4]=1[Cl:13])#[N:2]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 122329903-Methyl-1-pentyn-3-amine hydrochlorideHCID 190878853,5-Dichloro-4-cyanobenzoyl chloride

생성물 1

HCID 220676963,5-Dichloro-4-cyanobenzamide

시약·촉매·용매 1

HCID 962Water용매

실험 절차

To a well stirred mixture of 4-cyano-3,5-dichlorobenzoyl chloride (4.0 g, 0.017 mol) and water (100 ml) at 0° C. (ice-water bath) were added 3-amino-3-methyl-1-pentyne hydrochloride and 50 weight percent aqueous sodium hydroxide (10 ml). The resulting mixture was stirred 1 hour at 0° C., warmed up to room temperature and extracted with ethyl acetate (3×50 ml), the combined organic layers were washed with water (3×50 ml), and then dried over anhydrous sodium sulfate. The solvent was then eliminated in the rotavap, yielding the crude product as a yellow oil (2.79 g). The crude product was purified by Michel-Miller chromatographic column packed with Merck (grade 60) silica gel using ethyl acetate as solvent, yielding 0.75 g of N-[3'-methyl-1'-pentynyl)]-4-cyano-3,5-dichlorobenzamide.

후처리

  1. stirringThe resulting mixture was stirred 1 hour at 0° C.
  2. extractionextracted with ethyl acetate (3×50 ml)
  3. washthe combined organic layers were washed with water (3×50 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customyielding the crude product as a yellow oil (2.79 g)
  6. customThe crude product was purified by Michel-Miller chromatographic column

출처 및 근거

ORD 기록
ord-4c97cb8ba78e494395d3544731ab85ec
출처 데이터셋
uspto-grants-1994_04
특허 번호
US05304572

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