I add songs to itunes, but ipod will not update!

I imported songs onto my itunes library. But when I plug it in the usb to update, it will automatically disconnect after 5 minutes, and the ipod will not update. I've tried adding all music, and just checked songs; both do not not work.
I have version 7.0.0.7
I have about 50% of room left on my ipod.
Any suggestions??

Hello Rex225
The best way to resolve the issue is to remove the music from the iPhone and then download the purchase again using the steps in the following article.
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/ht2519
Thanks for using Apple Support Communities.
Regards,
-Norm G.

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