Ethanol → HCID 53932684, compound

HRID 366945Notes

Reaction equation

HRID 366945 reaction equation
[NH2:1][C:2]1[N:6]([C@H:7]2[O:13][C@@H:12]([CH2:14][OH:15])[C@H:10]([OH:11])[C@@H:8]2[OH:9])[N:5]=[CH:4][C:3]=1[C:16]#[N:17].OO.C([OH:22])C>[OH-].[NH4+]>[NH2:1][C:2]1[N:6]([C@H:7]2[O:13][C@@H:12]([CH2:14][OH:15])[C@H:10]([OH:11])[C@@H:8]2[OH:9])[N:5]=[CH:4][C:3]=1[C:16]([NH2:17])=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 784Hydrogen PeroxideHCID 53841639HCID 53841639, compound

Product 1

HCID 53932684HCID 53932684, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 14923Ammonium HydroxideSolvent

Procedure

To a solution of (25) (4.60 g) in ammonium hydroxide (35 mL) was added 30% hydrogen peroxide (2 mL). The mixture was stirred in a pressure bottle at room temperature for 18 h, the pressure bottle was cooled, opened carefully and the volatile products were evaporated to dryness. The residue thus obtained was co-evaporated with ethanol (3×20 mL). The crude product on crystallization with ethanol/water gave pure compound 3.5 g (71%): 1H NMR (DMSO-d6) δ 3.57 (m, 2H, C5'CH2), 3.86 (q, 1H, C4'H), 4.11 (q, 1H, C3'H), 4.43 (q, 1H, C2'OH), 5.63 (d, 1H, J=3.99 Hz, C1',H), 6.51 (br s, 2H, NH2), 6.71 and 7.26 (2br s, 2H, CONH2) and 7.69 (s, 1H, C3H). Anal. Calc. for C9H14N4O5 (258.23): C, 41.86; H, 5.46; N, 21.69. Found: C, 41.57; H, 5.40; N, 21.61.

Workup

  1. temperaturethe pressure bottle was cooled
  2. customthe volatile products were evaporated to dryness
  3. customThe residue thus obtained
  4. customThe crude product on crystallization with ethanol/water

Sources & evidence

ORD record
ord-4d80e09876e341498e9b559b0cefd913
Source dataset
uspto-grants-2000_10
Patent number
US06130326

Reaction notes

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