2-Bromobutane → HCID 21873384, compound

HRID 723349Notes

Reaction equation

HRID 723349 reaction equation
[CH3:1][N:2]([CH3:25])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[CH:16]=[CH:15][N:14]([C:17]3[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=3)[C:13]2=[O:24])=[CH:8][CH:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:32][CH:33](Br)[CH2:34][CH3:35]>C(#N)CC>[CH:33]([O:23][C:20]1[CH:19]=[CH:18][C:17]([N:14]2[CH:15]=[CH:16][N:12]([C:9]3[CH:8]=[CH:7][C:6]([O:5][CH2:4][CH2:3][N:2]([CH3:25])[CH3:1])=[CH:11][CH:10]=3)[C:13]2=[O:24])=[CH:22][CH:21]=1)([CH2:34][CH3:35])[CH3:32]

Participants

5

Reactant 3

HCID 65542-BromobutaneHCID 10796Cesium carbonateHCID 21873309HCID 21873309, compound

Product 1

HCID 21873384HCID 21873384, compound

Reagents, catalysts & solvents 1

HCID 7854PropionitrileSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1-[4-(2-dimethylaminoethoxy)phenyl]-3-(4-hydroxyphenyl)-1,3-dihydroimidazol-2-one (50 mg) in propionitrile (1 mL) was mixed with cesium carbonate (100 mg) and 2-butyl bromide (25 mg) and heated at 80° C. for 2 hours. The reaction solution was filtered and the concentrated. The residue was purified by preparative HPLC. The product with the molecular weight of 395.51 (C23H29N3O3); MS (ESI): 396 ([M+H]+), was obtained as hydrotrifluoroacetate in this way.

Workup

  1. filtrationThe reaction solution was filtered
  2. customThe residue was purified by preparative HPLC
  3. customMS (ESI): 396 ([M+H]+), was obtained as hydrotrifluoroacetate in this way

Sources & evidence

ORD record
ord-1d3df17bbc6b4bf783389d3842f8ecaf
Source dataset
uspto-grants-2006_11
Patent number
US07141561B2

Reaction notes

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