Methyl chloroformate → HCID 57594295, compound

HRID 1785064Notes

Reaction equation

HRID 1785064 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C@H:14]([NH:16][CH3:17])[CH3:15])[N:11]([CH3:13])[CH:12]=2)=[CH:4][CH:3]=1.Cl[C:19]([O:21][CH3:22])=[O:20].C([O-])([O-])=O.[Na+].[Na+].C1COCC1>O.CCOC(C)=O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C@H:14]([N:16]([CH3:17])[C:19](=[O:20])[O:21][CH3:22])[CH3:15])[N:11]([CH3:13])[CH:12]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 6586Methyl chloroformateHCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 57594721HCID 57594721, compound

Product 1

HCID 57594295HCID 57594295, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 250 mL round bottom flask was added (R)-1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)-N-methylethanamine (3.1 g, 9.1 mmol), methyl chloroformate (0.84 mL, 10.9 mmol), Na2CO3 (1.15 g, 10.9 mmol), and THF (100 mL). The reaction was stirred for 2 hours, followed by the addition of EtOAc (50 mL) and water (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to give 1.50 g (41%) of (R)-methyl 1-(4-(4-iodophenyl)-1-methyl-1H-imidazol-2-yl)ethyl(methyl)carbamate as an off-white solid (M+H (m/z)=400).

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. filtrationfiltered
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8a2a4d712e6a4a46ab05384dc8900b8d
Source dataset
uspto-grants-2009_03
Patent number
US07504413B2

Reaction notes

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