Synthesis of p-acetamidobenzenesulfonyl azide

Preparation of p-acetamidobenzenesulfonyl azide

Preparation of p-acetamidobenzenesulfonyl azide

Preparation of p-acetamidobenzenesulfonyl azide

To a mechanically stirred and ice bath cooled suspension of p-acetamidobenzenesulfonyl chloride (100 g, 0.430 mol) in methylene chloride (800 ml) containing 0.2 g tetraethylammonium chloride was added dropwise over 30 min a solution of sodium azide (70.7 g, 0.472 mol) in water (100 ml). The reaction mixture was allowed to attain room temperature over 3 hours and then stirred overnight. The organic layer was separated, washed with water (twice with 150 ml), saturated sodium chloride solution (twice with 150 ml), dried over magnesium sulfate and evaporated. The resultant tan solid was dissolved in toluene (3 crops totalling 1800 ml) keeping the solution below 80°C (steam bath). The toluene solutions were filtered and allowed to stand at room temperature. The resultant colorless prisms were collected, washed with petroleum ether (bp 35-65 ºC), and dried. Yield: 75.1 g (73%), mp 106-108°C. NMR (60 MHz, CDCl3) 6 2.3 (s, 3, CH3), 7.9 (bs, 4, aromatic), 8.3 (bs, 1, NH).

Baum, J. S.; Shook, D. A.; Davies, H. M. L.; Smith, H. D., Synth. Commun. 1987, 17, 1709.

Davies, H. M. L.; Cantrell, W. R.; Romines, K. R.; Baum, J. S., Org. Synth. 1992, 70, 93.

Cremlyn, R. J. W., J. Chem. Soc. 1965, 1132.

Curtius, T.; Stoll, W., J. Prakt. Chem. 1926, 112, 117.

Draganov, A.; Bozhinov, V., Dokl. Bulgar. 1987, 40,61(Chem. Abstr.
1988, 108, 186280t).

IUPAC Name

N-(4-azidosulfonylphenyl)acetamide

InChI

InChI=1S/C8H8N4O3S/c1-6(13)10-7-2-4-8(5-3-7)16(14,15)12-11-9/h2-5H,1H3,(H,10,13)

InChI Key

NTMHWRHEGDRTPD-UHFFFAOYSA-N

Canonical SMILES

CC(=O)NC1=CC=C(C=C1)S(=O)(=O)N=[N+]=[N-]

Depositor-Supplied Synonyms

4-Acetamidobenzenesulfonyl azide, 2158-14-7, p-ABSA, 4-acetamidobenzenesulphonyl azide, N-(4-azidosulfonylphenyl)acetamide, 4-acetamidobenzenesulfonylazide, 4-Acetamidobenzene sulfonyl azide, 4-acetamidobenzene-1-sulfonyl azide, ST50410723, ZINC04521086, ACMC-1CHYO, AC1NNY7H, AC1Q1KRA, SCHEMBL25234, C8H8N4O3S, KSC491C8R, p-acetamidobenzensulfonyl azide, 4-acetamidophenylsulfonyl azide, 4′-(Azidosulfonyl)acetoanilide, 4-acetamidobenzenesulphonylazide, 4-acetylaminobenzensulfonylazide, p-acetamidobenzenesulfonyl azide, 404764_ALDRICH, Jsp004384, p-acetamidobenzenesulphonyl azide, 4-Acetylaminobenzenesulfonylazide, 4-acetamido benzenesulfonyl azide, CTK3J1188, NTMHWRHEGDRTPD-UHFFFAOYSA-N, 4-acetylamino-benzenesulfonyl azide, 4-acetylamino-benzenesulphonyl azide, N-(4-azidosulfonylphenyl)ethanamide, NSC82543, ZINC4521086, 4-(acetylamino)benzene sulfonylazide, 4-(acetylamino)benzenesulfonyl azide, ANW-24500, NSC-82543, MCULE-7919140968, RP28424, RTR-010134, AJ-51362, AK-37852, AN-25646, CJ-12077, KB-36117, L610, NS-00009, OR006156, SC-21317, AB0014795, AB1007638, DB-028677, TR-010134, BB 0263019, FT-0617376, K-6159, A815501, 3B3-013362

Removed Synonyms

CID5129185, A1786, N-{4-[(diazoazamvinyl)sulfonyl]phenyl}acetamide

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