Triethylamine → HCID 21802382, 화합물

HRID 2379734노트

반응식

HRID 2379734 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([NH:19][CH:20]=O)([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.F[B-](F)(F)F.C([N+]1C2C=CC=CC=2OC=1Cl)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N+:19]#[C-:20])([CH2:15][CH2:16][CH2:17][CH3:18])[CH2:9][N:10]2[CH:14]=[N:13][CH:12]=[N:11]2)=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 27242402-Chloro-3-ethylbenzoxazolium tetrafluoroborateHCID 21802383HCID 21802383, 화합물

생성물 1

HCID 21802382HCID 21802382, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a stirred solution of 0.40 g (1.3 mmols) of N-[2-(4-chlorophenyl)-1-(1,2,4-triazol-1-yl)-2-hexyl]formamide in 5mL of methylene chloride under nitrogen was added 0.45 mL (3.26 mmols) of triethylamine. To this mixture was added a slurry of 0.439 g (1.63 mmols) of 3-ethyl-2-chlorobenzoxazolium tetrafluoroborate. which was weighed out under a nitrogen atmosphere, in 5 mL of methylene chloride. The reaction mixture was then allowed to stir at room temperature for 12 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The combined organic layers were washed once with 10% hydrochloric acid, brine, and dried over magnesium sutfate. Removal of solvents gave a crude oil which was purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane) to give 0.20 g (52%) of a clear, colorless oil. 1H-NMR 200 MHz (CDCl3, Me4Si) 0.8 (t, J=5 Hz, CH2 -CH3), 1.0-1.6 (m, 4H, 1.90-2.2 (m, 2H), 4.55 (ABq, J=16.8 Hz, JAB =15 Hz, CH2 -N), 7.2-7.5 (q, 4H, aromatic H), 7.9 (s CH=N), 8.0 ppm (s, CH=N).

후처리

  1. extractionextracted with ethyl acetate
  2. washThe combined organic layers were washed once with 10% hydrochloric acid, brine
  3. dry with materialdried over magnesium sutfate
  4. customRemoval of solvents
  5. customgave a crude oil which
  6. customwas purified by column chromatography (Merck 60 silica gel, ethyl acetate/hexane)
  7. customto give 0.20 g (52%) of a clear, colorless oil

출처 및 근거

ORD 기록
ord-33ec21be27824e94b78b69ce8cadcf7e
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05364870

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