Chlorosuccinimide → HCID 53728317, compound

HRID 1757186Notes

Reaction equation

HRID 1757186 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[CH:8][N:9]=1)[CH2:2][CH2:3][CH3:4].[Cl:31]N1C(=O)CCC1=O>O1CCCC1>[CH2:1]([C:5]1[N:6]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=2[Cl:30])[C:7]([CH2:10][CH:11]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]([O:14][CH3:15])=[O:13])=[C:8]([Cl:31])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 15284533HCID 15284533, compound

Product 1

HCID 53728317HCID 53728317, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 3-[2-n-butyl-1-{(2-chlorophenyl)methyl}-1H-imidazol-5-yl]-2-benzylpropanoate [Example 9 (4.34 g, 0.01 mol) in tetrahydrofuran (20 mL) was added N-chlorosuccinimide (1.35 g, 0.01 mol) in portions over a one hour period. The mixture was heated to 60° C. for one-hour. The tetrahydrofuran was evaporated, the residue was dissolved in ethyl-acetate and washed with 5% aqueous sodium bicarbonate solution and water. The dried, concentrated product was flash chromatographed over silica gel with 1:1 hexane/ethyl acetate to provide 2.7 g (55%) of the title compound.

Workup

  1. customover a one hour
  2. customThe tetrahydrofuran was evaporated
  3. dissolutionthe residue was dissolved in ethyl-acetate
  4. washwashed with 5% aqueous sodium bicarbonate solution and water
  5. customchromatographed over silica gel with 1:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-feb488e3fdeb497d8a612d82786feecb
Source dataset
uspto-grants-1995_08
Patent number
US05444080

Reaction notes

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