Dimethylformamide → 3,4-Thiophenediacetonitrile, 2,5-dimethyl-

HRID 900981

반응식

HRID 900981 반응식
[C-:1]#[N:2].[K+].Cl[CH2:5][C:6]1[C:10]([CH2:11]Cl)=[C:9]([CH3:13])[S:8][C:7]=1[CH3:14].C[N:16]([CH:18]=O)C>C(Cl)(Cl)Cl.[Na+].[Cl-]>[C:1]([CH2:5][C:6]1[C:10]([CH2:11][C:18]#[N:16])=[C:9]([CH3:13])[S:8][C:7]=1[CH3:14])#[N:2]

참가 물질

6

반응물 3

HCID 6228Dimethylformamide2회HCID 9032Potassium CyanideHCID 2883993,4-Bis(chloromethyl)-2,5-dimethylthiophene

생성물 1

HCID 8190183,4-Thiophenediacetonitrile, 2,5-dimethyl-수율 94.6%

시약·촉매·용매 2

HCID 5234Sodium Chloride용매HCID 6212Chloroform용매

반응 조건

온도
0 °C

실험 절차

A suspension of potassium cyanide (13.2 g, 203 mmol) in DMF (66 mL) is cooled to 0° C. and carefully treated with a solution of 3,4-bis-chloromethyl-2,5-dimethyl-thiophene (10.0 g, 48.0 mmol) in DMF (34 mL). After warming to room temperature and stirring for 18 h, the solution is heated to 40° C. for 1 h, cooled to room temperature and diluted with chloroform and saturated aq NaCl. The chloroform layer is separated, and the aq layer extracted with chloroform. The combined organic layers are washed with saturated aq NaCl, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue is triturated with heptane, filtered under vacuum and dried overnight in a vacuum oven to give (4-cyanomethyl-2,5-dimethyl-thiophen-3-yl)-acetonitrile (8.6 g, 94.6%) as an off-white solid: mp 123.5-125.5° C.; Rf 0.33 (30% ethyl acetate in heptane); 1H NMR (CDCl3, 300 MHz) δ 3.65 (s, 4 H), 2.38 (s, 6 H).

후처리

  1. temperatureAfter warming to room temperature
  2. temperaturethe solution is heated to 40° C. for 1 h
  3. temperaturecooled to room temperature
  4. customThe chloroform layer is separated
  5. extractionthe aq layer extracted with chloroform
  6. washThe combined organic layers are washed with saturated aq NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe resulting residue is triturated with heptane
  11. filtrationfiltered under vacuum
  12. customdried overnight in a vacuum oven

출처 및 근거

ORD 기록
ord-633078a22eba4766b2697327ca066b54
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07361671B2

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