Ethyl isocyanatoacetate → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(ethoxycarbonyl)methylurea

HRID 1884898

Reaction equation

HRID 1884898 reaction equation
[NH2:1][C:2]1[C:3]([OH:13])=[C:4]([S:9]([NH2:12])(=[O:11])=[O:10])[C:5]([Cl:8])=[CH:6][CH:7]=1.[N:14]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:15]=[O:16]>CN(C)C=O.C(OCC)(=O)C>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:15]([NH:14][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:16])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 76283Ethyl isocyanatoacetateHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 10154964N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-(ethoxycarbonyl)methylureaYield 7.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (170 mg, 0.76 mmol) and ethyl isocyanatoacetate (103 μL, 0.92 mmol) in 1.5 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. The mixture was diluted with ethyl acetate and washed with water to give the crude. Purification upon column chromatograph on silica gel, eluting with ethyl acetate/hexane (60/40, v/v), followed by Gilson HPLC separation, gave the desired product (20 mg, 7%). LC-MS (m/z) 352.0 (M+).

Workup

  1. washwashed with water
  2. customto give the crude
  3. customPurification upon column chromatograph on silica gel
  4. washeluting with ethyl acetate/hexane (60/40
  5. customv/v), followed by Gilson HPLC separation

Sources & evidence

ORD record
ord-f2518a3388a049b690f3d2beba0e13ec
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Linked notes

Loading…