To be of any assistance,
- Which version of Windows are you running?
- Which version of iTunes are you using?
- What is your iPod firmware/software version as shown in the iTunes summary page?
Error -50 occurs when iTunes tries to write data to your iPod, but was unsuscessful, due to unknown reason as the message say. Most likely cause the Window Registry for iTunes is corrupted, then the iTunes needs to be re-install. And your iPod firmware need to be updated.
So try this, do a Hard Reset as below
- After charging till full charge, at least 2 hours (preferably 4 hours)
- Toggle the Hold switch, make sure you dont see the red mark when you do the next step
- Reset the iPod -> Press Menu and Center button simultaneously for about 10 secs till the Apple Logo comes ON
- Then release the buttons
- Select your preferred language.
Here is the Apple support Article on the 5Rs
http://www.apple.com/support/ipod/five_rs/classic/
Then Re-install your iTunes
Put the iPod in Disk Mode
http://support.apple.com/kb/HT1363?viewlocale=en_US
Connect the iPod to a High Power USB 2.0 port at the back of your PC, and never use the USB Hub, or any USB port at the front of the PC.
Disconnect all other USB devices, except the mouse and keyboard.
Select the iPod in the Device pane of iTunes, and click Check for Updates
If it says "Software is uptodate", Press Restore just the same, although this will erase your iPod.
After Restore, Sync your iPod
Good Luck!