N,N-diethylthiophene-3-carboxamide → (Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)

HRID 2410243ノート

反応式

HRID 2410243 の反応式
C(N(CC)[C:4]([C:6]1[CH:10]=[CH:9][S:8][CH:7]=1)=[O:5])C>C1COCC1>[S:8]1[CH:9]=[CH:10][C:6]2[C:4](=[O:5])[C:7]3[S:8][CH:9]=[CH:10][C:6]=3[C:4](=[O:5])[C:7]1=2

参加物

3

反応物 1

HCID 11389776N,N-diethylthiophene-3-carboxamide

生成物 1

HCID 288478(Benzo(1,2-b:4,5-b)dithiophene-4,8-dione)

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

N,N-diethylthiophene-3-carboxamide (18.3 g, 0.1 mol) was dissolved in THF (100 mL) in a flame dried flask kept under an inert atmosphere. The reaction flak was placed in an ice bath followed by the dropwise addition of n-BuLi (40.0 mL, 2.5 M BuLi in hexane) over a period of 30 minutes. The reaction mixture was then allowed to warm to room temperature and stirred over a period of 2 hours. The reaction mixture was subsequently slowly poured into ice water (250 mL) and stirred for several hours. The resulting reaction mixture was filtered and the yellow precipitate washed successively with water, methanol (50 mL) and hexanes (50 mL). The title compound was obtained as a yellow powder (yield: 75%): GC-Ms: 220; 1H NMR (400 MHz, CDCl3,ppm) δ: 7.69-7.68(d, 2H), 7.65-7.64(d, 2H); 1H NMR (400 MHz, DMSO-d6, ppm) δ: 8.12-8.11(d, 2H), 7.60-7.59(d, 2H); 13C NMR (100 MHz, CDCl3, ppm) δ: 174.7, 145.1, 143.1, 133.8, 126.8.

後処理

  1. customdried flask
  2. customThe reaction flak was placed in an ice bath
  3. additionfollowed by the dropwise addition of n-BuLi (40.0 mL, 2.5 M BuLi in hexane) over a period of 30 minutes
  4. additionThe reaction mixture was subsequently slowly poured into ice water (250 mL)
  5. stirringstirred for several hours
  6. customThe resulting reaction mixture
  7. filtrationwas filtered
  8. washthe yellow precipitate washed successively with water, methanol (50 mL) and hexanes (50 mL)

出典と根拠

ORDレコード
ord-b9f613f3feaf4bbea178e1743e064318
出典データセット
uspto-grants-2014_08
特許番号
US08816035B2

反応ノート

読み込み中…