Triethylamine → (E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide

HRID 1272079노트

반응식

HRID 1272079 반응식
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:20][C:21]([NH:28][S:29]([CH:32]=[CH2:33])(=[O:31])=[O:30])([CH3:27])[CH2:22][C:23]([CH3:26])([CH3:25])[CH3:24].Br[C:35]1[S:36][CH:37]=[CH:38][CH:39]=1.C(N(CC)CC)C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:27][C:21]([NH:28][S:29](/[CH:32]=[CH:33]/[C:35]1[S:36][CH:37]=[CH:38][CH:39]=1)(=[O:31])=[O:30])([CH3:20])[CH2:22][C:23]([CH3:24])([CH3:25])[CH3:26]

참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 138512-BromothiopheneHCID 17748074N-(2,4,4-Trimethylpentan-2-yl)ethenesulfonamide

생성물 1

HCID 86609959(E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide수율 21.2%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

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온도
140 °C

실험 절차

Palladium acetate (169 mg, 0.75 mmol) and triphenylphosphine (420 mg, 1.6 mmol) were added to a solution of ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (10 g, 45.7 mmol) and 2-bromo-thiophene (3.74 mL, 39.1 mmol) in N,N-dimethylformamide (75 mL). Triethylamine (14.7 mL, 105.5 mmol) was added and the mixture was flushed with nitrogen and heated at 140° C. for 16 hours. The mixture was cooled to room temperature and 1N HCl (250 mL) was added in one portion. The mixture was extracted with ethyl acetate (3×200 mL) and the combined organics were dried over MgSO4, filtered and concentrated in vacuo to afford a solid. The solid was purified by dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate). The fractions were combined to afford (E)-2-thiophen-2-yl-ethenesulfonic acid (1,1,3,3-tetramethyl-butyl)-amide (2.5 g, 21% yield).

후처리

  1. customthe mixture was flushed with nitrogen
  2. temperatureThe mixture was cooled to room temperature
  3. addition1N HCl (250 mL) was added in one portion
  4. extractionThe mixture was extracted with ethyl acetate (3×200 mL)
  5. dry with materialthe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto afford a solid
  9. customThe solid was purified
  10. dry with materialby dry flash chromatography (SiO2, heptane to 1:1 heptane: ethyl acetate)

출처 및 근거

ORD 기록
ord-e5cb5e604a2448f2bf735eeb2dc98a01
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208506B2

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