Bromotrichloromethane → HCID 57550204, compound

HRID 1716847Notes

Reaction equation

HRID 1716847 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[O:19][CH2:20][CH:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=2)=[CH:14][CH:13]=1.BrC(Cl)(Cl)Cl.C1CCN2C(=NCCC2)CC1>C(Cl)Cl>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[O:19][CH:20]=[C:21]([C:23]([O:25][CH3:26])=[O:24])[N:22]=2)=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6383BromotrichloromethaneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57550206HCID 57550206, compound

Product 1

HCID 57550204HCID 57550204, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of methyl {2-{4-[(1-methyl-1H-benzimidazol-2-yl)methyl]-phenyl}-4,5-dihydro-1,3-oxazol-4-yl}carboxylate (1.5 g, 5 mmol) in CH2Cl2 was treated with bromotrichloromethane (1.22 g, 6 mmol) and DBU (0.70 g, 4.6 mol), stirred at room temperature overnight and concentrated in vacuo. The resultant residue was purified by column chromatography (silica, CHCl3:MeOH 1%) to give the title compound in 15% yield, identified by NMR and mass spectral analyses. 1H NMR (400 MHz, CDCl3): 8.2 (s, 1H), 8.06 (d, J=8.0 Hz, 2H), 7.3 (d, J=8.0 Hz, 2H), 7.27 (m, 4H), 4.3 (s, 2H), 3.95 (s, 3H), 3.63 (s, 3H). LCMS (ESI+) 348 (MH+).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue was purified by column chromatography (silica, CHCl3:MeOH 1%)

Sources & evidence

ORD record
ord-2bb01ab171c04691a197b90a3f9615c6
Source dataset
uspto-grants-2010_09
Patent number
US07803825B2

Reaction notes

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