Isopropyl isocyanate → N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-isopropylurea

HRID 1884895Notes

Reaction equation

HRID 1884895 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.[CH:14]([N:17]=[C:18]=[O:19])([CH3:16])[CH3:15]>CN(C)C=O.C(OCC)(=O)C>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:18]([NH:17][CH:14]([CH3:16])[CH3:15])=[O:19])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 61277Isopropyl isocyanateHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9879637N-(3-aminosulfonyl-4-chloro-2-hydroxyphenyl)-N'-isopropylureaYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (150 mg, 0.67 mmol) and isopropyl isocyanate (80 μL, 0.81 mmol) in 1 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 (50/50, v/v), followed by recrystallization from acetone and hexane, gave the desired product (111 mg, 54%). LC-MS (m/z) 308.0 (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 (50/50
  5. customv/v), followed by recrystallization from acetone and hexane

Sources & evidence

ORD record
ord-92b81b6ab7844d85accde8dc18b1ffd7
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Reaction notes

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