반응식
[C:1]([C:5]1[CH:6]=[C:7]([CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])[CH:8]=O)([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[C:20]([CH2:24][NH2:25])[CH:19]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:32]([O:34][P:35]([O-:39])[O:36][CH2:37][CH3:38])[CH3:33]>C1C=CC=CC=1.CO>[C:1]([C:5]1[CH:6]=[C:7]([C:8]2[C:22]([CH2:23][NH:18][CH2:19][P:35](=[O:39])([O:36][CH2:37][CH3:38])[O:34][CH2:32][CH3:33])=[CH:21][CH:20]=[CH:24][N:25]=2)[CH:10]=[C:11]([C:14]([CH3:17])([CH3:16])[CH3:15])[C:12]=1[OH:13])([CH3:4])([CH3:3])[CH3:2]참가 물질
반응물 4
생성물 1
시약·촉매·용매 2
실험 절차
A mixture of 5.0 g (21.4 mmol) of 3,5-di-t-butyl-4-hydroxy benzaldehyde, 2.34 g (21.6 mmol) of 3-picolylamine and 6.0 g (42.8 mmol) anhydrous potassium carbonate in 50 ml benzene was refluxed for one day. The potassium carbonate was filtered and the solvent was evaporated. The residue was heated at 140° C. with 3.0 g (21.6 mmol) of diethylphosphite for 3 h. An amount of 6.6 g of compound was isolated by column chromatography (95/5 CHCl13 /MeOH), which gave 5.9 g (60%) after recrystallization in petroleum ether; mp=100°-101 ° C. IR (film): 3650 cm-1 :OH, 3300 (large): NH, 1430: tert-Bu, 1230: P=O, 1030: P--O--C, NMR (CDCl3): δ=8.50, 7.65 and 7.25 (3 m, 4H): aromatic H, 3-picolyl 7.20 (d, JP-H =2 Hz, 2H): aromatic H, 3,5-di-butyl-4-hydroxyphenyl 5.25 (s, 1H): OH 4.08, 3.94 and 3.80 (3m, 4H): P--O--CH2CH3 3.91 (d, JP-H =19 Hz, 1H): CH--PO3Et2 3.81 and 3.61 (2d, J=13 Hz, 2H): NH--CH2 --Py 2.20 (broad): NH-, 1.45 (s, 18H): tert-Bu 1.30 and 1.10 (2t, J=7 Hz, 6H): P--O--CH2CH3MS: m/e=462: M+, 324:M+ --HPO3Et2 (base peak) Elemental analysis C25H39N2O4P % Calc C 64.91 H 8.50 N 6.06 P 6.70 % Found C 64.83 H 8.70 N 5.88 P 6.45
후처리
- temperaturewas refluxed for one day
- filtrationThe potassium carbonate was filtered
- customthe solvent was evaporated
출처 및 근거
- ORD 기록
- ord-dad972b096f042feaccf6ee8b4c647ec
- 출처 데이터셋
- uspto-grants-1995_06
- 특허 번호
- US05424303
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