Water → HCID 16222501, compound

HRID 856977Notes

Reaction equation

HRID 856977 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]=[C:11]([C:13]3[NH:14][CH:15]=[CH:16][C:17]=3[Cl:18])[O:10][N:9]=2)=[CH:4][CH:3]=1.IC.[C:21](=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Cl:18][C:17]1[CH:16]=[CH:15][N:14]([CH3:21])[C:13]=1[C:11]1[O:10][N:9]=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:12]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 135446371HCID 135446371, compound

Product 1

HCID 16222501HCID 16222501, compoundYield 37.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of 3-(4-chloro-phenyl)-5-(3-chloro-1H-pyrrol-2-yl)-[1,2,4]-oxadiazole (30.0 mg, 0.11 mmol), iodomethane (0.08 ml, 0.17 mmol) and potassium carbonate (23 mg, 0.17 mmol) in dimethylformamide (2 ml) was heated at 85° C. for 4 h. It was diluted by water (20 ml) and the mixture was extracted by EtOAc. The extracts were evaporated, and the residue was purified by column chromatography (EtOAc: Hexane=1:1) to give 12.0 mg (37%) of the title compound. 1H NMR (CDCl3): 8.11–8.07 (m, 2H), 7.50–7.45 (m, 2H), 6.84 (d, J=3.0 Hz, 1H), 6.28 (d, J=3.3 Hz, 1H), 4.08 (s, 3H).

Workup

  1. extractionthe mixture was extracted by EtOAc
  2. customThe extracts were evaporated
  3. customthe residue was purified by column chromatography (EtOAc: Hexane=1:1)

Sources & evidence

ORD record
ord-9ba7ede350c74589af76d7cc1e8903d4
Source dataset
uspto-grants-2006_12
Patent number
US07144876B2

Reaction notes

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