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

HRID 900981

反応式

HRID 900981 の反応式
[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]

参加物

6

反応物 3

HCID 6228Dimethylformamide2 回HCID 9032Potassium CyanideHCID 2883993,4-Bis(chloromethyl)-2,5-dimethylthiophene

生成物 1

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

試薬・触媒・溶媒 2

HCID 5234Sodium Chloride溶媒HCID 6212Chloroform溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-633078a22eba4766b2697327ca066b54
出典データセット
uspto-grants-2008_04
特許番号
US07361671B2

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