Please provide a detailed mechanism (with arrows) for this reaction.

Organic Chemistry
8th Edition
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Chapter27: Amino Acids And Proteins
Section: Chapter Questions
Problem 27.39P: A chemically modified guanidino group is present in cimetidine (Tagamet), a widely prescribed drug...
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Please provide a detailed mechanism (with arrows) for this reaction. 

Scheme 2. Synthesis of Sulfathiazole
dry CH3CN,
K2CO3
HCI
CI-
NHCOCH3
+
-NHCOCH3
-NH2
NH2 reflux, 25 min
reflux, 30 min
4-acetamidobenzenesulfonyl chloride
2-aminothiazole
p-acetamidobenzenesulfonamide
sulfathiazole
Transcribed Image Text:Scheme 2. Synthesis of Sulfathiazole dry CH3CN, K2CO3 HCI CI- NHCOCH3 + -NHCOCH3 -NH2 NH2 reflux, 25 min reflux, 30 min 4-acetamidobenzenesulfonyl chloride 2-aminothiazole p-acetamidobenzenesulfonamide sulfathiazole
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