USB is probably not very suitable for what you want to do.
USB is asymmetric, meaning a USB connection has a host on one end and a peripheral device on the other end. (For example, when you connect a USB drive to a PC, the PC is the host, and the stick is peripheral.) The host initiates and controls the data transfer.
An Android phone usually acts as a peripheral device. Starting with Android 3.1, the phone can also act as a USB host, although not all phones support this.
In order to accomplish what you mean, the PC will need to run a piece of software that changes it from host mode to peripheral mode and provides some kind of storage that the Android device could record.
Bluetooth may be the best option for you. You can simply initiate the file transfer via Bluetooth immediately after changing the file. Inexpensive Bluetooth USB dongles are available for PCs without Bluetooth support. You may need some software on your PC if you want to automatically accept the request to transfer files to your PC.
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