N-Iodosuccinimide → HCID 67207989, compound

HRID 1253489Notes

Reaction equation

HRID 1253489 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[C:7]1[S:8][CH:9]=[CH:10][CH:11]=1.C1C(=O)N([I:19])C(=O)C1>C(#N)C.C(OCC)(=O)C>[I:19][C:6]1[N:2]([CH3:1])[C:3]([C:7]2[S:8][CH:9]=[CH:10][CH:11]=2)=[N:4][CH:5]=1

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 151298991-Methyl-2-(thiophen-2-yl)-1H-imidazole

Product 1

HCID 67207989HCID 67207989, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 1-methyl-2-(2-thienyl)-1H-imidazole (116 mg, 0.706 mmol) in acetonitrile (5 ml) was added NIS (159 mg, 0.706 mmol) at room temperature. The reaction mixture was heated in the Biotage Initiator Series microwave for 1 hour at 120° C. The reaction mixture was diluted in ethyl acetate, washed with 1N aqueous sodium hydroxide and brine then dried over sodium sulfate, filtered and concentrated to give 5-iodo-1-methyl-2-(2-thienyl)-1H-imidazole. The material was taken forward without any additional purification. LRMS (ESI) calculated for C8H8N2SI [M+H]+, 290.9; found 291.0.

Workup

  1. washwashed with 1N aqueous sodium hydroxide and brine
  2. dry with materialthen dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ae9ffc160390419e964a891bd80e5871
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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