2-(Ethoxymethylene)propanedinitrile → HCID 57504673、化合物

HRID 1098202ノート

反応式

HRID 1098202 の反応式
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]

参加物

5

反応物 3

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

生成物 1

HCID 57504673HCID 57504673、化合物収率 19.11%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-a37c234b992e4b6faf5089a38d80470a
出典データセット
uspto-grants-2012_03
特許番号
US08143263B2

反応ノート

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