Dimethylformamide → 4-(2',6'-Dimethylphenoxy)phthalonitrile

HRID 409217

反応式

HRID 409217 の反応式
[N+]([C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9])([O-])=O.[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[OH:22].C([O-])([O-])=O.[K+].[K+].CN(C=O)C>O>[CH3:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[C:16]=1[O:22][C:4]1[CH:5]=[C:6]([C:12]#[N:13])[C:7](=[CH:10][CH:11]=1)[C:8]#[N:9]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 113352,6-DimethylphenolHCID 11430Potassium CarbonateHCID 974431,2-Benzenedicarbonitrile, 4-nitro-

生成物 1

HCID 9520734-(2',6'-Dimethylphenoxy)phthalonitrile収率 87%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

A mixture of 4-nitro-phthalonitrile (1 eq), 2,6-dimethylphenol (1.2 eq), K2CO3 (2 eq), and DMF (1 mL/mmol 4-nitro-phthalonitrile) was heated under nitrogen at 60° C. for 3 h with stirring. After cooling to ambient temperature the mixture was poured into water (6 mL/mL DMF) with stirring. The mixture was extracted twice with EtOAc. The combined organic phases were dried over MgSO4 and concentrated in vacuo. The residue was recrystallized from EtOH to give the title compound as a tan solid (yield: 87%); 1H NMR (CDCl3, 200 MHz): δ=7.70 (d, 1H), 7.05 to 7.16 (m, 5H), 2.08 (s, 6H).

後処理

  1. temperatureAfter cooling to ambient temperature the mixture
  2. stirringwith stirring
  3. extractionThe mixture was extracted twice with EtOAc
  4. dry with materialThe combined organic phases were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from EtOH

出典と根拠

ORDレコード
ord-9978a0cb1dd743ffa8a7648d2010ff6b
出典データセット
uspto-grants-2014_06
特許番号
US08759373B2

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