Ethyl chloroformate → HCID 19002976, compound

HRID 1728328Notes

Reaction equation

HRID 1728328 reaction equation
[CH3:1][C:2]1[NH:3][C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH2:7][CH3:8])[N:6]=1.[H-].[Na+].[CH2:18]([O:20][C:21](Cl)=O)[CH3:19]>CN(C)C=O>[CH2:18]([O:20][CH2:21][N:3]1[C:4]([S:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[C:5]([CH2:7][CH3:8])[N:6]=[C:2]1[CH3:1])[CH3:19]

Participants

5

Reactant 3

HCID 10928Ethyl chloroformateHCID 24758Sodium hydrideHCID 178437673HCID 178437673, compound

Product 1

HCID 19002976HCID 19002976, compoundYield 64.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 500 mg of 4-ethyl-2-methyl-5-phenylthioimidazole 2 (2.3 mmol ) obtained in Example 1 (2) in 5 ml of dry dimethylformamide is added 140 mg of 60% oil suspension of sodium hydride (3.5 mmol) under ice cooling. Five minutes later, 330 mg of ethoxycarbonyl chloride (3.5 mmol) is added to the mixture, which is stirred for 15 minutes. The reaction mixture is poured onto ice water and extracted with ethyl ether. The extract is washed with water, dried over sodium sulfate, filtered and the filtrate is concentrated. The residue is chromatographed on a column of silica gel, eluting with ethyl acetate/n-hexane (2:1) to give 410 mg of the desired product I-2 as an oil. Yield, 65%.

Workup

  1. additionThe reaction mixture is poured onto ice water
  2. extractionextracted with ethyl ether
  3. washThe extract is washed with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated
  7. customThe residue is chromatographed on a column of silica gel
  8. washeluting with ethyl acetate/n-hexane (2:1)

Sources & evidence

ORD record
ord-5aa3444589cb4e45b8a3ad61051e9166
Source dataset
uspto-grants-1994_07
Patent number
US05326780

Reaction notes

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