127-76-4

Basic information

• Product Name: 4'-(thiazol-2-ylsulphamoyl)acetanilide
• Synonyms: 4'-(thiazol-2-ylsulphamoyl)acetanilide;N4-Acetylsulfathiazole;N-(2-Thiazolyl)-4-(acetylamino)benzenesulfonamide;N-(Thiazole-2-yl)-4-(acetylamino)benzenesulfonamide;N-[4-[(2-Thiazolylamino)sulfonyl]phenyl]acetamide;p-Acetylamino-N-(2-thiazolyl)benzenesulfonamide;N-[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]acetamide;N-[4-(1,3-thiazol-2-ylsulfamoyl)phenyl]ethanamide
• CAS NO: 127-76-4
• Molecular Formula: C₁₁H₁₁N₃O₃S₂
• Molecular Weight: 297.35334
• EINECS: 204-864-1
• Mol File: 127-76-4.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 505.14℃[at 101 325 Pa]
• Appearance: /
• Density: 1.4558 (rough estimate)
• Vapor Pressure: 0Pa at 25℃
• Refractive Index: 1.6740 (estimate)
• Storage Temp.: 2-8°C
• Water Solubility: 0.1g/L(37 oC)
• CAS DataBase Reference: 4'-(thiazol-2-ylsulphamoyl)acetanilide(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-(thiazol-2-ylsulphamoyl)acetanilide(127-76-4)
• EPA Substance Registry System: 4'-(thiazol-2-ylsulphamoyl)acetanilide(127-76-4)

Safety Data

• Hazardous Substances Data: 127-76-4(Hazardous Substances Data)

Usage

Definition

ChEBI: A sulfonamide that is benzenesulfonamide substituted by an acetylamino group at position 4 and a 1,3-thiazol-2-yl group at the nitrogen atom. It is a metabolite of sulfathiazole.

Flammability and Explosibility

Notclassified

Synthetic route

2-bromo-1,3-thiazole (3034-53-5) + p-acetylaminobenzenesulfonamide (121-61-9) → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With copper; potassium carbonate at 200℃;

2-thiazolylamine (96-50-4) + p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
at 130℃;
With ethyl acetate
With pyridine

Sulfathiazole (72-14-0) → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With acetic anhydride; acetic acid
With pyridine; acetyl chloride

1,4-dithiane-2,5-diol (40018-26-6) + calcium salt of N-acetyl-sulfanilic acid-cyanamide → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With hydrogenchloride

1,2-dichloroethyl acetate (10140-87-1) + sodium-salt of -thiourea → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With water; sodium acetate

1,2-dichloro-2-ethoxyethane (623-46-1) + sodium-salt of -thiourea → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With water

p-acetylaminobenzenesulfonyl chloride (121-60-8) + thiazol-2-ylamine-<2-chloro-toluene-4-sulfonate> → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
With pyridine; acetone

water (7732-18-5) + 4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide (2183-24-6) + diethylamine (109-89-7) → N4-acetyl-N1-diethylsulfanilamide (2080-32-2) + 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

p-acetylaminobenzenesulfonyl chloride (121-60-8) → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate; sodium chloride / water; acetone / 2.5 h / 25 - 30 °C 2: ammonium hydroxide / water; acetone / 2.5 h / 65 °C View Scheme

N,N-bis(4-acetamidobenzenesulfonyl)-2-aminothiazole → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + p-acetylaminobenzenesulfonamide (121-61-9)

Conditions	Yield
With ammonium hydroxide In water; acetone at 65℃; for 2.5h;

Acetanilid (103-84-4) → 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: chlorosulfonic acid / Heating 2: potassium carbonate / acetonitrile / Reflux View Scheme

1-bromo-butane (109-65-9) + 4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → N-acetyl-sulfanilic acid-(3-butyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With sodium hydroxide; potassium iodide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + N-acetyl-sulfanilic acid isopropyl ester (64704-17-2) → sulfanilic acid-(3-isopropyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With ethanol; guanidine nitrate Erhitzen des Reaktionsprodukts mit wss. HCl;

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + benzyl bromide (100-39-0) → N-acetyl-sulfanilic acid-(3-benzyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With sodium hydroxide; potassium iodide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + benzyl chloride (100-44-7) → N-acetyl-sulfanilic acid-(3-benzyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With 1,4-dioxane; sodium hydrogencarbonate at 120℃;

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + propyl bromide (106-94-5) → N-acetyl-sulfanilic acid-(3-propyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + 4-chlorobenzenesulfonyl chloride (98-60-2) → 4-acetylamino-N-[3-(4-chloro-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide

Conditions	Yield
With pyridine

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + 2-(diethylamino)ethyl chloride (100-35-6) → N-acetyl-sulfanilic acid-[3-(2-diethylamino-ethyl)-3H-thiazol-2-ylidenamide]

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + chloroacetic acid (79-11-8) → [2-(N-acetyl-sulfanilylimino)-thiazol-3-yl]-acetic acid ethyl ester

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + 2-Chloro-N,N-diethylacetamide (2315-36-8) → [2-(N-acetyl-sulfanilylimino)-thiazol-3-yl]-acetic acid diethylamide

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + benzenesulfonyl chloride (98-09-9) → 4-acetylamino-N-(3-benzenesulfonyl-3H-thiazol-2-ylidene)-benzenesulfonamide (103096-38-4)

Conditions	Yield
With sodium hydrogencarbonate; acetone
With pyridine

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + p-toluenesulfonyl chloride (98-59-9) → sulfanilic acid-[3-(toluene-4-sulfonyl)-3H-thiazol-2-ylidenamide]

Conditions	Yield
With 1,4-dioxane; sodium hydrogencarbonate

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + dimethyl sulfate (77-78-1) → 4-acetylamino-N-(3-methyl-3H-thiazol-2-ylidene)-benzenesulfonamide (66507-94-6)

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + i-pentyl bromide (107-82-4) → N-acetyl-sulfanilic acid-(3-isopentyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With sodium hydroxide; potassium iodide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + 2-bromoethanol (540-51-2) → N-acetyl-sulfanilic acid-[3-(2-hydroxy-ethyl)-3H-thiazol-2-ylidenamide]

Conditions	Yield
With sodium hydroxide; potassium iodide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + 2-bromoallyl bromide (513-31-5) → N-acetyl-sulfanilic acid-[3-(2-bromo-allyl)-3H-thiazol-2-ylidenamide]

Conditions	Yield
With sodium hydroxide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → Sulfathiazole (72-14-0)

Conditions	Yield
With hydrogenchloride
With sodium hydroxide
With sodium hydroxide In water at 65℃; for 2h;

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → N-acetyl-sulfanilic acid-(3-ethyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
With sodium hydroxide; ethyl bromide; potassium iodide

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → 2-[(N-acetyl-sulfanilyl)-amino]-2,3-dihydro-thiazole-2-sulfonic acid ; sodium-salt

Conditions	Yield
With water; sodium hydrogensulfite

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) + dimethyl sulfate (77-78-1) + aqueous NaOH → 4-acetylamino-N-(3-methyl-3H-thiazol-2-ylidene)-benzenesulfonamide (66507-94-6)

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → sulfanilic acid-(3-ethyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
Multi-step reaction with 2 steps 1: ethyl bromide; KI; aqueous NaOH 2: aqueous HCl View Scheme

4'-(thiazol-2-ylsulfamoyl)acetanilide (127-76-4) → sulfanilic acid-(3-propyl-3H-thiazol-2-ylidenamide)

Conditions	Yield
Multi-step reaction with 2 steps 1: aqueous NaOH 2: aqueous HCl View Scheme

Upstream product

• 96-50-4 2-thiazolylamine 
• 121-60-8 p-acetylaminobenzenesulfonyl chloride 
• 40018-26-6 1,4-dithiane-2,5-diol 
• 10140-87-1 1,2-dichloroethyl acetate 
• 623-46-1 1,2-dichloro-2-ethoxyethane 
• 7732-18-5 water 
• 2183-24-6 4-acetylamino-N-[3-(4-acetylamino-benzenesulfonyl)-3H-thiazol-2-ylidene]-benzenesulfonamide 
• 109-89-7 diethylamine 
• 103-84-4 Acetanilid 
• 72-14-0 Sulfathiazole 
• 3034-53-5 2-bromo-1,3-thiazole 
• 121-61-9 p-acetylaminobenzenesulfonamide 

Downstream Products

• 103096-38-4 4-acetylamino-N-(3-benzenesulfonyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 66507-94-6 4-acetylamino-N-(3-methyl-3H-thiazol-2-ylidene)-benzenesulfonamide 
• 72-14-0 Sulfathiazole 
• 93722-28-2 4-amino-N-[3-(2-diethylamino-ethyl)-3H-thiazol-2-ylidene]-benzenesulfonamide 

Relevant articles and documents

Synthesis, antimicrobial, and docking investigations of remarkably modified sulfathiazole derivatives

SOME new sulfathiazole derivatives were synthesized. The sulfathiazole starting material was reacted with ethyl bromoacetate and gave unpredictably an ester product 2. The substitution occurred selectively at the tautomeric proton of the NH thiazolyl nitrogen rather than the aromatic NH2 protons. The ester was further hydrazinolysed followed by condensation with several aldehydes to establish hydrazones (4a-h). Hantzesch thiazole synthesis was also applied to build antimicrobial agents containing multi-thiazole moieties. The structures of the synthesized compounds were confirmed by 1H, 13C, 2D 1H NMR, MS, and microanalyses. The synthesized compounds were tested for their antimicrobial activity towards Gram-positive and Gram-negative bacteria, and fungi strains. Some of the investigated compounds showed prominent high potency. The docking study revealed the mode of action between the modified sulfathiazole ligands and the binding site of DHPS.