IPod Classic 80GB stops Synchronization after 2500 Songs

I have got an iPod Classic 6th Gen with 80 GB and Software version 1.1.2. I use the newest iTunes version and Windows 7 x64.
I recently resetted the iPod and wanted to sync my complete library to the iPod again. But now it always fails to finish the synchronization. After ca. 2500 songs the process bar does not proceed anymore and on the iPod display it says "Connected" instead of "Synchronizing". If I wait a few minutes iTunes throws an Error "Copy failed; please check your CD drive or internet connection" (I use the german version, so this might not be the original text). If I click OK on this error a warning appears like: "iTunes could not copy song X to iPod, due to unknown reason (-53)". If i unplug the iPod it has about 200-300 songs on it. When I unplug the iPod before the error popup appears, it has 0 songs on it. When I reconnect the iPod it says there are 0GB music but 5-10GB other data on the iPod (this yellow bar; seems that he thinks, that the synchronized music files are something else than music).
When I synchronize the iPod maually and select less than 2500 songs the synchronization usually works. But if I start adding songs the same error as above will occur sooner or later.
I tried this with different iTunes versions and different operationg systems (Win 7 and XP) I even tried synchronizing with Windows Media Player and the Dopisp plugin. The error always occurs when i synchronize more than 2500 songs (one time I got at least 4500). I already tried it more than 20 times. I resetted the iPod via iTunes; formatted it, deleted my library and added the songs again, synchronized step by step (Sync about 100 songs, wait to finish, than sync the next 100 songs, ...), nothing helped.
Can someone please help me?

DragonBall,
I don't have my ipod with me to check this, but I beleive when I disconnect my headphones, the ipod pauses. I have seen several complaints about pauses and hesitations. When I get home I am gong to play with this for a few minutes. The point I am getting to the long way around is, if you have a bad connection at the headphones, electrically that could be very close to the same thing as disconnecting your headphones. When it pauses, is the ipod being moved, like walking around with the cable wagging around. Also, if I understand correctly, you are using the same set of headphones with both units that are doing the same thing. Don't know if this will solve your problem, but good luck.
Message was edited by: david-iPod80Gb

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