Imidazole → 4-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

HRID 1670816Notes

Reaction equation

HRID 1670816 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Br:20]Br.N1C=CN=C1.[CH:27]1([CH:33]([CH2:48][CH2:49]O)[C:34]([NH:36][CH2:37][C:38]2[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=2[Cl:47])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(Cl)Cl>[Br:20][CH2:49][CH2:48][CH:33]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1)[C:34]([NH:36][CH2:37][C:38]1[C:43]([Cl:44])=[CH:42][C:41]([O:45][CH3:46])=[CH:40][C:39]=1[Cl:47])=[O:35]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 11776TriphenylphosphineHCID 24408BromineHCID 673553892-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide

Product 1

HCID 673563304-bromo-2-cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-butyramide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Stir a mixture of triphenylphosphine (3.16 g, 12.06 mmol), bromine (1.91 g, 12.06) and methylene chloride (150 mL) at room temperature for 20 minutes. To the mixture, add a solution of imidazole (0.98 g, 14.48 mmol), 2-Cyclohexyl-N-(2,6-dichloro-4-methoxy-benzyl)-4-hydroxy-butyramide (4.5 g, 12.06 mmol) in methylene chloride (100 mL). Stir the reaction at room temperature for 3.5 hours. Wash the reaction with HCl (1 N), water and brine. After drying the organic layer over sodium sulfate, filter and concentrate under vacuum. Purify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane to afford 2.5 g. of the title compound. MS (m/z): 436 (M+H)+.

Workup

  1. stirringStir
  2. customthe reaction at room temperature for 3.5 hours
  3. washWash
  4. customthe reaction with HCl (1 N), water and brine
  5. dry with materialAfter drying the organic layer over sodium sulfate
  6. filtrationfilter
  7. concentrationconcentrate under vacuum
  8. customPurify the residue by silica gel chromatography with 1:3 ethyl acetate/hexane
  9. customto afford 2.5 g

Sources & evidence

ORD record
ord-cddb05a3e0884bed93a66cbb2603130f
Source dataset
uspto-grants-2011_08
Patent number
US07994176B2

Reaction notes

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