West Indies, after bowling out Bangladesh for 161 to earn a first innings lead of 219, closed on 208-4.
Left-hander Chanderpaul, in his 158th test, struck five fours off 98 balls. He shared an undefeated fifth-wicket stand of 108 with rookie Jermaine Blackwood, who compiled 43 not out. The right-hander hit a four and a six off 96 deliveries.
The innings had earlier been anchored by Kraigg Brathwaite (45) and Leon Johnson (41) in an opening stand of 76.
Mahmudullah, who hit a top-score of 53 in Bangladesh’s innings, returned to grab 2-37 with his off-spin. There was a wicket apiece for seamer Shafiul Islam (1-21) and left-arm spinner Taijul Islam (1-76).
The West Indies, leading 1-0 in the two-match series, encountered dogged resistance from Mahmudullah and the lower order when Bangladesh started the day on 104-7.
All-rounder Mahmudullah stretched his frustrating eighth-wicket stand with Shafiul to 45 before the West Indies finally broke through.
Mahmudullah became the 11th Bangladeshi to 1,000 test runs when he reached 32 but soon lost Shafiul, who edged through to wicket-keeper Denesh Ramdin off the persevering Shannon Gabriel (1-49). Shafiul resisted for 50 deliveries in making 10.
That dismissal energized Mahmudullah, who smacked a six over midwicket off Gabriel and brought up his half century with his second four.
But left-arm spinner Sulieman Benn ended his 161-minute vigil soon afterward as he edged a cut to give Ramdin his fifth catch of the innings.
Benn quickly added the scalp of Robiul Islam (0), lbw sweeping, to finish with 2-19.
The West Indies, whose healthy advantage had been set up by fast bowler Kemar Roach (5-42) on day two, opted not to enforce the follow on, and Brathwaite and Johnson soon consolidated the hosts’ supremacy.
The pair, which added 143 in the first innings, seemed set for another century stand when Bangladesh struck back either side of tea to stall the West Indies’ progress.
Johnson, on debut, hit eight fours in 41 off 59 balls before he yorked himself as he advanced down the pitch to Taijul.
That wicket boosted Bangladesh and Shafiul added the scalp of Kirk Edwards for 2. Out-of-form Edwards deflected a low catch to gully.
Brathwaite and Darren Bravo laboured in a partnership of 16 before both fell to Mahmudullah in the final session.
Bravo (7) was bowled off the inside edge and back pad while Brathwaite, after hitting three fours and his first six in test cricket, edged to first slip.
At 100-4, the innings was at the crossroads but 40-year-old Chanderpaul, in his typically unfussed manner, and right-hander Blackwood, 18 years his junior, defied Bangladesh for the rest of the day.