Trimethylsilyl iodide → HCID 57320184, compound

HRID 2301605Notes

Reaction equation

HRID 2301605 reaction equation
C([O:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:16]([OH:34])=[C:17]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21])(=[O:14])=[O:13])C1C=CC=CC=1.I[Si](C)(C)C>ClCCl>[OH:8][CH2:9][CH2:10][NH:11][S:12]([C:15]1[C:16]([OH:34])=[C:17]([NH:22][C:23]([NH:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[C:27]=2[Cl:33])=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21])(=[O:14])=[O:13]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 69824934HCID 69824934, compound

Product 1

HCID 57320184HCID 57320184, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[3-[N″-(2-benzyloxyethyl)aminosulfonyl]4-chloro-2-hydroxyphenyl]-N′-(2,3-dichlorophenyl) urea (46 mg, 0.08 mmol) in 3mL of dichloromethane was added iodotrimethylsilane (38 mg, 0.19 mmol). The mixture was stirred for 16 hours at room temperature. Purification by column chromatography on silica gel, eluting with ethyl acetate/hexane (60/40, v/v), gave the desired product (14 mg, 37%). LC-MS (m/z) 455.8 (M+).

Workup

  1. customPurification by column chromatography on silica gel
  2. washeluting with ethyl acetate/hexane (60/40

Sources & evidence

ORD record
ord-f75ccef6f0d54895869b4b16c2463442
Source dataset
uspto-grants-2002_12
Patent number
US06500863B1

Reaction notes

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