Ethanol → HCID 11709978, compound

HRID 601466Notes

Reaction equation

HRID 601466 reaction equation
[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[C:6](=[O:19])[N:5]([CH2:20][CH2:21][CH3:22])[C:4](=[O:23])[CH:3]=1.O.C(O)C.[N:28]([O-])=[O:29].[Na+]>C(O)(=O)C>[NH2:1][C:2]1[N:7]([CH2:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=2)[C:6](=[O:19])[N:5]([CH2:20][CH2:21][CH3:22])[C:4](=[O:23])[C:3]=1[N:28]=[O:29]

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 11500685HCID 11500685, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 11709978HCID 11709978, compoundYield 96.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 232 gm of crude 6-amino-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil (4), 4.0 L of water and ca. 2.0 L of ethanol at 80 degrees C. was added 55.3 gm of sodium nitrite in one portion, followed by the dropwise addition of 100 mL of glacial acetic acid. After stirring at 80 degrees C. for 20 minutes the mixture was allowed to cool to near room temperature, then was chilled in an ice bath to effect crystallization. The solids were isolated by filtration, washed with two 1.0 L portions of water and dried under vacuum to yield 244 gm of purple colored 6-amino-5-nitroso-1-[2-(4-nitrophenyl)ethyl]-3-propyluracil (5).

Workup

  1. customat 80 degrees C
  2. temperatureto cool to near room temperature
  3. temperaturewas chilled in an ice bath
  4. customcrystallization
  5. customThe solids were isolated by filtration
  6. washwashed with two 1.0 L portions of water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-2b5eeb63a01c4926bbbba8e792b727a8
Source dataset
uspto-grants-2011_03
Patent number
US07902360B2

Reaction notes

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