Cyclopentyl Isocyanate → HCID 9902202, compound

HRID 432611Notes

Reaction equation

HRID 432611 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]1([N:19]=[C:20]=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15]1>CN(C)C=O>[NH2:12][S:9]([C:4]1[C:3]([OH:13])=[C:2]([NH:1][C:20]([NH:19][CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)=[O:21])[CH:7]=[CH:6][C:5]=1[Cl:8])(=[O:11])=[O:10]

Participants

4

Reactant 2

HCID 643500Cyclopentyl IsocyanateHCID 113680593-Amino-6-chloro-2-hydroxy-benzenesulfonamide

Product 1

HCID 9902202HCID 9902202, compoundYield 43.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-6-chloro-2-hydroxybenzenesulfonamide (200 mg, 0.90 mmol) and cyclopentyl isocyanate (100 mg, 0.90 mmol) in 1.5 mL of N,N-dimethyl-formamide was stirred at room temperature for 20 hours. Purification upon column chromatograph on silica gel, eluting with ethyl acetate/hexane (20/80, v/v), followed by recrystallization from diethyl ether and hexane, gave the desired product (130 mg, 43%). LC-MS (m/z) 334.2 (M+).

Workup

  1. customPurification upon column chromatograph on silica gel
  2. washeluting with ethyl acetate/hexane (20/80
  3. customv/v), followed by recrystallization from diethyl ether and hexane

Sources & evidence

ORD record
ord-13ecad7074be4f05b077ea343140f422
Source dataset
uspto-grants-2003_12
Patent number
US06664259B2

Reaction notes

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