Chlorosuccinimide → HCID 59251291, compound

HRID 1046637Notes

Reaction equation

HRID 1046637 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[CH:10]=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:12]=2)=[C:4]([Cl:25])[CH:3]=1.[Cl:26]N1C(=O)CCC1=O>CC#N>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:17]3[C:22]([Cl:23])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:24])[C:10]([Cl:26])=[C:11]([C:13]([OH:16])([CH3:15])[CH3:14])[N:12]=2)=[C:4]([Cl:25])[CH:3]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 59251315HCID 59251315, compound

Product 1

HCID 59251291HCID 59251291, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 2-[2-(4-bromo-2-chlorophenyl)-1-(2,6-dichlorophenyl)-1H-imidazol-4-yl]-propan-2-ol (230 mg, 0.50 mmol) in MeCN (4 mL, anhyd) was charged with N-chlorosuccinimide (70 mg, 0.52 mg) and then heated at 70 C. After 22 h the reaction mixture was charged with additional N-chlorosuccinimide (67 mg, 0.50 mmol) and heated at 85 C. After 40 h (total reaction time) the reaction mixture was allowed to cool to ambient temperature, concentrated and purified by chromatography (silica, EtOAc/Hex, 0:100 to 30:70) to give the title compound (0.19 g, 77%) as a white solid. 1H-NMR (DCM-d2): δ 7.61 (d, 1H), 7.42-7.45 (m, 2H), 7.36 (m, 1H), 7.27 (dd, 1H), 7.10 (d, 1H), 3.33 (s, 1H), 1.65 (s, 6H).

Workup

  1. temperatureheated at 70 C
  2. temperatureheated at 85 C
  3. concentrationconcentrated
  4. custompurified by chromatography (silica, EtOAc/Hex, 0:100 to 30:70)

Sources & evidence

ORD record
ord-29fb038d79374737b38cd9cf4d9e2d85
Source dataset
uspto-grants-2013_10
Patent number
US08569352B2

Reaction notes

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