Triethylamine → HCID 21802382、化合物

HRID 2379734ノート

反応式

HRID 2379734 の反応式
[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

参加物

5

反応物 3

HCID 8471TriethylamineHCID 27242402-Chloro-3-ethylbenzoxazolium tetrafluoroborateHCID 21802383HCID 21802383、化合物

生成物 1

HCID 21802382HCID 21802382、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-33ec21be27824e94b78b69ce8cadcf7e
出典データセット
uspto-grants-1994_11
特許番号
US05364870

反応ノート

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