Water → (2E)-2-Chloro-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

HRID 1441343Notes

Reaction equation

HRID 1441343 reaction equation
I(Cl)(=O)=O.I([Cl:8])(=O)=O.C([N+](C)(C)C)C1C=CC=CC=1.[CH3:20][N:21]([CH3:35])/[CH:22]=[CH:23]/[C:24]([C:26]1[N:30]([CH:31]([CH3:33])[CH3:32])[C:29]([CH3:34])=[N:28][CH:27]=1)=[O:25].O.C(=O)([O-])O.[Na+]>CO.C(Cl)Cl.C(Cl)Cl>[Cl:8]/[C:23](=[CH:22]/[N:21]([CH3:20])[CH3:35])/[C:24]([C:26]1[N:30]([CH:31]([CH3:32])[CH3:33])[C:29]([CH3:34])=[N:28][CH:27]=1)=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 22273494(E)-3-(Dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-oneHCID 56924451Trimethylbenzylammonium Dichloroiodate

Product 1

HCID 86613527(2E)-2-Chloro-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

Benzyltrimethylammonium dichloroiodate (2.6 g 7.5 mmol) was added in portions to a stirred solution of (2E)-3-(dimethylamino)-1-(1-isopropyl-2-methyl-1H-imidazol-5-yl)prop-2-en-1-one (Method 24 of WO 03/076436; 1.1 g 5 mmol) in MeOH/DCM (15/30 ml) at room temperature. After 1 hour water (10 ml) and DCM (20 ml) were added followed after a further 30 minutes by saturated sodium hydrogen carbonate solution (20 ml). The organics were separated, re-extracted the aqueous with DCM (25 ml). The combined organics were washed with 5% (w/v) sodium thiosulphate solution (30 to 35 ml) and brine (25 ml), dried (Na2SO4) and evaporated to give the title compound as an oil (crude yield 1.68 g still wet). M/z 256.

Workup

  1. customThe organics were separated
  2. extractionre-extracted the aqueous with DCM (25 ml)
  3. washThe combined organics were washed with 5% (w/v) sodium thiosulphate solution (30 to 35 ml) and brine (25 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-73a5bbb1eef84a20868a79f94586fda3
Source dataset
uspto-grants-2010_02
Patent number
US07655652B2

Reaction notes

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