Propyl isocyanate → HCID 9922625, compound

HRID 1884897Notes

Reaction equation

HRID 1884897 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.[CH2:14]([N:17]=[C:18]=[O:19])[CH2:15][CH3:16]>CN(C)C=O.C(OCC)(=O)C>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:18]([NH:17][CH2:14][CH2:15][CH3:16])=[O:19])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

5

Reactant 2

HCID 61033Propyl isocyanateHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9922625HCID 9922625, compoundYield 44.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (150 mg, 0.67 mmol) and propyl isocyanate (76 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 (92 mg, 44%). LC-MS (m/z) 308.2 (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-490bc5ee11ae4a9294ffe8ca8c598b97
Source dataset
uspto-grants-2004_07
Patent number
US06767922B2

Reaction notes

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