"Leaving the Village" (里抜け, Sato Nuke) is episode 444 of the Naruto: Shippūden anime.
Sasuke knocks Izumo and Kotetsu out on his way out of Konoha. He is intercepted by Kakashi, who asks what he is doing. Sasuke thanks him for his training, but explains he is unsatisfied with his progress, revealing he is going to train with Orochimaru, and incapacitates Kakashi with genjutsu. Upon waking up, Kakashi relays the information to Hiruzen, Minato, and Tsunade, herself informing the others about Jiraiya's intel regarding Orochimaru's imminent need for a new vessel. Sakura overhears their conversation. Minato wants to handle the situation internally as discreetly as possible, to avoid worsening the already delicate situation with the Uchiha, and orders a lockdown. The Konoha 11 meet up at the Academy at night, where Sakura and Shikamaru inform the others about Sasuke's departure. Naruto and Shikamaru sneak out of the village through a tunnel created by Kiba, and Naruto promises Sakura to bring Sasuke back. Neji notices someone else sneaking out as well. Kushina informs Minato that Naruto and Shikamaru have escaped the lockdown. Naruto and Shikamaru are attacked by RootAnbu members Anko Mitarashi, Sai, Hayate Gekkō, and Yūgao Uzuki. They are sent by Danzō to ensure no one interferes with Sasuke reaching Orochimaru. Team Guy intercepts the attack. As the fight goes on, Shikamaru realises these are not regular Anbu. Sasuke continues on his way to Orochimaru.
There is an animation error when during the flashback of Naruto and his classmates back at the academy, the students wore headbands before they graduated.