2-(Ethoxymethylene)propanedinitrile → HCID 57504673, 화합물

HRID 1098202노트

반응식

HRID 1098202 반응식
C(O[CH:4]=[C:5]([C:8]#[N:9])[C:6]#[N:7])C.Cl.[F:11][C:12]1[CH:13]=[CH:14][C:15]([CH3:20])=[C:16]([NH:18][NH2:19])[CH:17]=1.C(N(CC)C(C)C)(C)C>CO>[NH2:9][C:8]1[N:18]([C:16]2[CH:17]=[C:12]([F:11])[CH:13]=[CH:14][C:15]=2[CH3:20])[N:19]=[CH:4][C:5]=1[C:6]#[N:7]

참가 물질

5

반응물 3

HCID 671522-(Ethoxymethylene)propanedinitrileHCID 81531DiisopropylethylamineHCID 17390099(5-Fluoro-2-methylphenyl)hydrazine--hydrogen chloride (1/1)

생성물 1

HCID 57504673HCID 57504673, 화합물수율 19.11%

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

(Ethoxymethylene)malononitrile (CAS no. 123-06-8) (3.18 g, 26.04 mmol) was added portionwise to the stirred solution of (5-fluoro-2-methylphenyl)hydrazine hydrochloride (CAS no. 325-50-8) (4.6 g, 26.04 mmol) and N,N-diisopropylethylamine (5.90 mL, 33.86 mmol) in MeOH (50 mL), under nitrogen at 5° C. The resulting solution was allowed to stir for a further 30 minutes at this temperature. The reaction mixture was then heated to reflux and was stirred for 3 hours. The reaction mixture was allowed to cool to ambient temperature. The reaction mixture was evaporated to dryness, redissolved in EtOAc (200 mL), washed with water (50 mL), and saturated brine (50 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product. This was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane to afford the product (1.076 g, 19.11%). 1H NMR (400 MHz, DMSO) δ 2.00 (3H, s), 6.56 (2H, s), 7.20 (1H, dd), 7.29 (1H, td), 7.43 (1H, t), 7.75 (1H, s); m/z (ES+) (M+H)+=217; HPLC tR=1.61 min.

후처리

  1. customat 5° C
  2. temperatureThe reaction mixture was then heated
  3. temperatureto reflux
  4. stirringwas stirred for 3 hours
  5. customThe reaction mixture was evaporated to dryness
  6. dissolutionredissolved in EtOAc (200 mL)
  7. washwashed with water (50 mL), and saturated brine (50 mL)
  8. dry with materialThe organic layer was dried (MgSO4)
  9. filtrationfiltered
  10. customevaporated
  11. customto afford crude product
  12. customThis was purified by flash silica chromatography, elution gradient 0 to 50% EtOAc in isohexane

출처 및 근거

ORD 기록
ord-a37c234b992e4b6faf5089a38d80470a
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08143263B2

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