m-Chloroperbenzoic acid → HCID 45260703, compound

HRID 1816240Notes

Reaction equation

HRID 1816240 reaction equation
[NH:1]1[CH2:5][CH2:4][N:3]=[C:2]1[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14][CH3:15].[Cl:16]C1C=C(C=CC=1)C(OO)=[O:21]>ClCCl>[ClH:16].[NH:3]1[CH2:4][CH2:5][N:1]=[C:2]1[CH2:6][NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[S:14]([CH3:15])=[O:21]

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 11108001HCID 11108001, compound

Product 1

HCID 45260703HCID 45260703, compoundYield 76.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-(4,5-Dihydro-1H-imidazol-2-ylmethyl)-2-(methylthio)aniline (32 mg, 0.144 mmol, prepared as described in Example 1) was stirred in dichloromethane (1 mL) and treated with m-chloroperoxybenzoic acid (35 mg of 70 wt %). After 15 minutes the mixture was evaporated and treated with ether (2 mL), 3 drops of methanol, and then 1N HCl in ether (0.2 mL). The resulting precipitate was collected and washed with ether (1 mL) to give N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-2-(methylsulfinyl)aniline hydrochloride salt (30 mg).

Workup

  1. customAfter 15 minutes the mixture was evaporated
  2. additiontreated with ether (2 mL), 3 drops of methanol
  3. customThe resulting precipitate was collected
  4. washwashed with ether (1 mL)

Sources & evidence

ORD record
ord-40cb4167311e47a59312eb1321454a02
Source dataset
uspto-grants-2005_04
Patent number
US06884801B1

Reaction notes

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