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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 432609Generated: October 26, 2026

Dimethylformamide → N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N'-(4-methyl-cyclohexyl) urea

https://huagongshe.com/reaction/432609

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant4-Methylcyclohexanecarboxylic acidHCID 20330—
ReactantP,P-Diphenylphosphinic azideHCID 199401—
Reactant3-Amino-6-chloro-2-hydroxy-benzenesulfonamideHCID 11368059—
ProductN-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N'-(4-methyl-cyclohexyl) ureaHCID 9968924—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a solution of 4-Methyl-cyclohexanecarboxylic acid (0.141 mL) in DMF (0.5 mL) was added DPPA (0.215 mL) and TEA (0.139 mL) and the reaction heated at 80° C. After 18 hrs, 3-Amino-6-chloro-2-hydroxy-benzenesulfonamide (0.150 g) was added and the reaction heated at 80° C. After 18 hrs, the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layers were dried over anhydrous magnesium sulfate, and concentraed under reduced pressure. The crude residue was purified via HPLC to give 15 mg of N-[4-chloro-2-hydroxy-3-sulfamylphenyl]-N′-(4-methyl-cyclohexyl) urea. LC-MS (m/z) 347 (M+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06664259B2
Source datasetuspto-grants-2003_12
ORD IDord-e00e51ccbea146c6b400862721699a3e
Source noteuspto-grants-2003_12