4-(4-MethylphenylsulfonaMido)benzoic acid synthesis

7synthesis methods

Product Name:4-(4-MethylphenylsulfonaMido)benzoic acid
CAS Number:37028-85-6
Molecular formula:C14H13NO4S
Molecular Weight:291.32

150-13-0 Synthesis

150-13-0
950 suppliers
$5.00/25g

98-59-9 Synthesis

98-59-9
625 suppliers
$9.00/5g

4-(4-MethylphenylsulfonaMido)benzoic acid

37028-85-6
22 suppliers
$55.00/250mg

Yield:37028-85-6 98%

Reaction Conditions:

with sodium carbonate in water at 25; pH=8; for 2 h;

Steps:

5.2. Synthesis of 4-(toluene-4-sulfonylamino)-benzoic acid (3)

To a solution of p-amino benzoic acid (100 mmol, 13.71 g) and water (50 mL), sodium carbonate (1 N) was added to adjust the pH 8. Then added p-toluenesulfonyl chloride (120 mmol, 22.87 g) and the mixture was stirred at room temperature keeping the pH of the mixture up to 8.0 with occasional addition of sodium carbonate solution. Progress and completion of the reaction was confirmed by TLC and conversion of suspension into clear solution. After 2 h, whole mixture was poured into a beaker and the pH was adjusted to 2.0 by 1 N HCl. White precipitates were produced which were filtered and washed with distilled water. Colorless crystals were produced after recrystallization from methanol.Yield 98%, mp 231 °C; (Lit. mp 230 °C).²⁷ Anal. Calcd for C₁₄H₁₃NO₄S: C, 57.72; H, 4.50; N, 4.81; S, 11.01. Found: C, 57.36; H, 4.52; N, 4.83; S, 10.98. IR (KBr), cm^-1: 1117 (SO₂), 1334(SO₂), 1705 (CO), 3215 (OH) 3585 (NH). ¹H NMR (300 MHz, CDCl₃: CD₃OD): δ (ppm) = 2.24 (s, 3H, CH₃), 7.02 (d, J = 8.4 Hz, 2H, Ar-H), 7.11 (d, J = 8.1 Hz, 2H, Ar-H), 7.58 (d, J = 8.1 Hz, 2H, Ar-H), 7.76 (d, J = 8.4 Hz, 2H, Ar-H), 9.43 (s, 1H, NH).

References:

Mustafa, Ghulam;Khan, Islam Ullah;Ashraf, Muhammad;Afzal, Iftikhar;Shahzad, Sohail Anjum;Shafiq, Muhammad [Bioorganic and Medicinal Chemistry,2012,vol. 20,# 8,p. 2535 - 2539] Location in patent:experimental part

158038-67-6 Synthesis