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

HRID 2410243노트

반응식

HRID 2410243 반응식
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

참가 물질

3

반응물 1

HCID 11389776N,N-diethylthiophene-3-carboxamide

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-b9f613f3feaf4bbea178e1743e064318
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08816035B2

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