YOU SAID:

When my friend I died I was sad.

INTO JAPANESE

私の友人は私が死んだときは悲しかった。

BACK INTO ENGLISH

When a friend of mine died I was sad.

INTO JAPANESE

私の友人が死んだときは悲しかった。

BACK INTO ENGLISH

It was sad when my friend died.

INTO JAPANESE

私の友人が死んだときは悲しかった。

BACK INTO ENGLISH

It was sad when my friend died.