N-Iodosuccinimide → HCID 69477137, compound

HRID 1183201Notes

Reaction equation

HRID 1183201 reaction equation
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([C@H:13]3[CH2:15][C@@H:14]3[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:9][CH:8]=2)[N:4]=[CH:3]1.[I:21]N1C(=O)CCC1=O>ClCCl>[I:21][C:6]1[N:2]([CH3:1])[CH:3]=[N:4][C:5]=1[C:7]1[CH:8]=[CH:9][C:10]([C@H:13]2[CH2:15][C@@H:14]2[C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 86664897HCID 86664897, compound2×

Product 1

HCID 69477137HCID 69477137, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Ethyl (1S,2S)-2-[4-(1-methyl-1H-imidazol-4-yl)phenyl]cyclopropanecarboxylate (product of Step 1, 2.8 g, 10.36 mmol) in dichloromethane (104 mL) was added N-iodosuccinimide (2.1 g, 9.33 mmol). The reaction mixture was stirred at it for 16 h. The mixture was diluted with dichloromethane and washed with aqueous sodium thiosulfate, followed by three washes with water then dried (MgSO4). The solvent was concentrated to afford the title compound as an orange oil which could be used in the next Step without further purification. LCMS: [M+1]+=396.

Workup

  1. washwashed with aqueous sodium thiosulfate
  2. dry with materialthen dried (MgSO4)
  3. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-0d8178f556cf4adab3b2ca97cc6c3d3b
Source dataset
uspto-grants-2014_03
Patent number
US08664253B2

Reaction notes

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