Okay, main question here is what do you mean by 400 engine? Do you mean the Farmall 400's C281, or a 400-series diesel engine commonly used in 66, 86, and 88 series tractors from 1973 up?
The C281 engine may bolt up with minor modifications because I suspect that the bell housing bolt pattern is the same; a 660 is just a 560 with a revved-up engine and planetary gear reductions at the rear wheels. You'll need to drill holes in the frame rails for the front engine mounts, and figure out all the fuel, electrical, and gauge hookups.
The problem with a C281 engine is that it only turns 1800RPM, while the 660's stock engine turns 2800 RPM. Ground speed will be unbearably slow; you will probably be able to plow in road gear. I suppose you could put a pulling-modified governor on the Farmall 400 engine to get the RPMs back but don't expect to use it for work unless you like rebuilding engines.
If you're talking about a D414/D436/D466, then it's going to be a huge project. Look for a D360 out of a mid '80s school bus or municipal truck if you want to put a modern diesel in the tractor.
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Today's Featured Article - History of the Cockshutt Tractor - by Danny Bowes (Dsl). The son of a very successful Toronto and Brantford, Ontario merchant, and himself quite an entreprenuer, James G. Cockshutt opened a business called the Brantford Plow Works in 1877. In 1882, the business was incorporated to become the Cockshutt Plow Company. Along with quality built equipment, expedious demand and expansion made Cockshutt Plow Works the leader in the tillage tools sector of the farm equipment industry by the 1920's.
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