Can't manually copy song from iTunes library to iPod Touch

I just purchased 2 songs from the iTunes store. I've alway set my iTunes to allow me to manually manage my songs. When I drug the first song from the iTunes library to the iPod Touch, it went fine. When I drug the second one across it, it said it was copying the file and then when it got to the very end the beach ball came up and it never finished. I had to force quit. The second and subsequent times that I have tried to copy the song, I just get the endless beach ball. This is on a 2011 iMac running 10.7.5 and iTunes 12.0.1.26.

OK, I got it to work. I updated iTunes to 12.1. Rebooted the iMac, reconnected the iTouch and tried dragging the song from my iTunes library to the iTouch again. This time it copied OK. I'm not sure why.

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