Ethanol → HCID 488934, compound

HRID 2417227Notes

Reaction equation

HRID 2417227 reaction equation
COC1C=CC([O:9][CH2:10][CH2:11][O:12][CH2:13][N:14]2[C:22]3[C:17](=[N:18][CH:19]=[N:20][C:21]=3[NH2:23])[N:16]=[CH:15]2)=CC=1.O=[N+]([O-])[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[O-][N+](=O)[O-].[Ce+4].[NH4+].[NH4+].CCO>CC#N.O>[OH:9][CH2:10][CH2:11][O:12][CH2:13][N:14]1[C:22]2[C:17](=[N:18][CH:19]=[N:20][C:21]=2[NH2:23])[N:16]=[CH:15]1

Participants

6

Reactant 3

HCID 702EthanolHCID 180504Ceric ammonium nitrateHCID 11012503HCID 11012503, compound

Product 1

HCID 488934HCID 488934, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 14 (0.74 g, 3.54 mmol) was prepared in 80% yield from 13 (1.39 g, 4.43 mmol) and CAN (2.43 g, 4.43 mmol) in CH3CN (30 mL) and water (10 mL) by the method used for the synthesis of 9: mp 122-123° C.; Rf(hexanes/EtOAc=1:2) 0.12; UV (EtOH) λmax 265 (ε 14,800); 1H NMR (CD3OD) δ 3.69-3.79 (m, 4 H, O(CH2)2O), 5.79 (s, 2 H, H2C1′), 8.32 (s, 1 H, HC2), 8.60 (s, 1 H, HC8); 13C NMR (CD3OD) δ 61.80 (CH2OH), 72.27 (OCH2) 82.01 (C1′), 119.62 (C5), 144.29 (C2), 147.68 (C8), 150.32 (C4), 152.12 (C6); MS m/z 209 (M+). Anal (C8H11N5O2) C, H, N; calcd (%): 45.93, 5.30, 33.48; found (%): 45.80, 5.45, 33.51.

Workup

  1. customused for the synthesis of 9

Sources & evidence

ORD record
ord-7d8a4764c3fb4f2ea3ba7e6fa6798058
Source dataset
uspto-grants-2004_11
Patent number
US06825348B2

Reaction notes

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