Diethanolamine → 3,5-Difluoro-4-[bis(2-hydroxyethyl)amino]benzonitrile

HRID 23608

反応式

HRID 23608 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([F:11])[C:9]=1F)[C:5]#[N:6].[NH:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15]>CN(C)C(=O)C>[F:11][C:8]1[CH:7]=[C:4]([CH:3]=[C:2]([F:1])[C:9]=1[N:12]([CH2:16][CH2:17][OH:18])[CH2:13][CH2:14][OH:15])[C:5]#[N:6]

参加物

4

反応物 2

HCID 8113DiethanolamineHCID 5938143,4,5-Trifluorobenzonitrile

生成物 1

HCID 225901583,5-Difluoro-4-[bis(2-hydroxyethyl)amino]benzonitrile

試薬・触媒・溶媒 1

HCID 31374Dimethylacetamide溶媒

実験手順

A solution of 3,4,5-trifluorobenzonitrile (5 g, 32 mmol) and diethanolamine (6 ml, 85 mmol) in N,N-dimethylacetamide was stirred for 10 days. The solvent was then evaporated, the residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml), the organic layer dried (MgSO4) and evaporated to dryness. The residue was chromatographed using CH2Cl2-EtOAc as eluent to give, after recrystallization from toluene, 2.7 g (35%) of pure white crystals: mp 63-65° C.; 1H NMR δ3.33 (t, 4H, NCH2, J=6 Hz), 3.48 (t, 4H, OCH2, J=6 Hz), 4.43 (bs, 2H, OH), 7.57 (dd, 2H, H2+6, JH2, F3 and H6, F5=8.5 Hz, JH2, F5 and H6, F3=2Hz=22 Hz); 19F NMR δ −116.0 (d, 2F, F3+5, JF3, H2 and F5, 6=7.5 Hz); MS m/z 265 (M+Na+, 10), 243 (M+H+, 100), 211 (M-CH2OH, 85). Anal. (C11H12N2O2F2) C,H,N.

後処理

  1. customThe solvent was then evaporated
  2. customthe residue partitioned between CH2Cl2 (200 ml) and H2O (200 ml)
  3. dry with materialthe organic layer dried (MgSO4)
  4. customevaporated to dryness
  5. customThe residue was chromatographed
  6. customto give
  7. customafter recrystallization from toluene, 2.7 g (35%) of pure white crystals

出典と根拠

ORDレコード
ord-c0611c5f8c5b4b40ae10354cd46eeab6
出典データセット
uspto-grants-2005_02
特許番号
US06852755B1

関連ノート

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