Ethyl Acetate → HCID 885050, compound

HRID 1796665Notes

Reaction equation

HRID 1796665 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[SH:7].[H-].[Na+].[Cl:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1F.CCOC(C)=O>C1COCC1>[Cl:10][C:11]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:12]=1[S:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 676882-Chloro-1-fluoro-4-nitrobenzeneHCID 178480602HCID 178480602, compound

Product 1

HCID 885050HCID 885050, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-methyl-1H-imidazole-2-thiol (1.14 g, 10 mmol) in THF (50 ml) under argon at 0° C. was treated with NaH (303 mg, 11.98 mmol). The mixture was warmed to rt. A solution of 2-chloro-1-fluoro-4-nitro-benzene (1.76 g, 10 mmol) in THF (50 ml) was added, and the mixture was stirred at 70° C. for 4 h, cooled to rt. Treated with EtOAc (100 ml), the mixture was washed with H2O (2×25 ml), 1N KOH (30 ml) and brine (20 ml), dried with Na2SO4. Removal of the solvent under reduced pressure gave a yellow solid. Recrystalization of the solid in CH2Cl2/hexanes gave 426A (2.31 g, 86%) as a slight yellowish solid. It has a retention time of 3.99 min (standard LC1 method, 8 min run). MS Found: (M+H)+=270.1

Workup

  1. temperaturecooled to rt
  2. washthe mixture was washed with H2O (2×25 ml), 1N KOH (30 ml) and brine (20 ml)
  3. dry with materialdried with Na2SO4
  4. customRemoval of the solvent under reduced pressure
  5. customgave a yellow solid
  6. customRecrystalization of the solid in CH2Cl2/hexanes

Sources & evidence

ORD record
ord-29e2e9bcc79647e7aaa603b4c1707c5f
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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