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Water → 2-t-Butyl-5-cyano-1-nitrobenzene

HRID 1418191
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HRID 1418191 반응식
N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30](=O)[NH2:31])=[CH:26][C:25]=1[N+:33]([O-:35])=[O:34])([CH3:23])([CH3:22])[CH3:21].O>O1CCCC1.CCCCCC>[C:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][C:25]=1[N+:33]([O-:35])=[O:34])([CH3:23])([CH3:21])[CH3:22]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 1049PyridineHCID 9845Trifluoroacetic anhydrideHCID 19348480HCID 19348480, 화합물

생성물 1

HCID 107033622-t-Butyl-5-cyano-1-nitrobenzene수율 96.5%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매
HCID 8058
Hexane
용매

실험 절차

3.3 ml of pyridine and then 4.3 ml of trifluoroacetic anhydride were added to a solution of 2.25 g (10.1 mmol) of 2-t-butyl-5-carbamoyl-1-nitrobenzene [prepared as described in Preparation 38(i)] in 20 ml of tetrahydrofuran, and the resulting mixture was stirred for 20 minutes. The reaction mixture was then mixed with water, and the aqueous mixture was extracted with a mixture of ethyl acetate and hexane. The extract was washed with water and with a saturated aqueous solution of sodium chloride, after which it was dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 50 g of silica gel to give 1.99 g (yield 96%) of the title compound as crystals, melting at 70.5°-71.5° C. (from hexane).

후처리

  1. extractionthe aqueous mixture was extracted with a mixture of ethyl acetate and hexane
  2. washThe extract was washed with water and with a saturated aqueous solution of sodium chloride
  3. dry with materialafter which it was dried over anhydrous sodium sulfate
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified by column chromatography through 50 g of silica gel

출처 및 근거

ORD 기록
ord-8862bac8dfb741eb90d578890d6e8e7e
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05880147

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