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

HRID 409217

반응식

HRID 409217 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-9978a0cb1dd743ffa8a7648d2010ff6b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759373B2

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