Ethyl Acetate → HCID 3775205, compound

HRID 2072668Notes

Reaction equation

HRID 2072668 reaction equation
[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([OH:9])=O.S(Cl)(Cl)=O.C(OCC)(=O)C.[NH2:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]([CH3:32])[CH2:24][C:25]2([CH3:31])[CH3:30]>C(N(CC)CC)C>[CH3:1][C:2]1[N:3]=[CH:4][S:5][C:6]=1[C:7]([NH:20][C:21]1[CH:29]=[CH:28][CH:27]=[C:26]2[C:22]=1[CH:23]([CH3:32])[CH2:24][C:25]2([CH3:31])[CH3:30])=[O:9]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 2098054-Methylthiazole-5-carboxylic acidHCID 112175411,1,3-Trimethylindan-4-amine

Product 1

HCID 3775205HCID 3775205, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 1.7 g (10.3 mmols) of 4-methyl-5-thiazole carboxylic acid and 10 ml of thionyl chloride was refluxed for 1 hour. The reaction solution was distilled under reduced pressure to remove excess thionyl chloride. The residue was dissolved in 10 ml ethyl acetate. The solution was added to 10 ml of an ethyl acetate solution of 1.8 g (10.3 mmols) of 4-amino-1,1,3-trimethylindane and 4 ml of triethylamine, and the resultant solution was stirred at room temperature for 3 hours. The solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine. The solution was dried with magnesium sulfate and then concentrated under reduced pressure. The concentrated residue was separated and purified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/2), to obtain 1.6 g of amorphous solid substance (Compound No. 6 shown in Table 4). The yield was 50.2%.

Workup

  1. temperaturewas refluxed for 1 hour
  2. distillationThe reaction solution was distilled under reduced pressure
  3. customto remove excess thionyl chloride
  4. dissolutionThe residue was dissolved in 10 ml ethyl acetate
  5. washThe solution was washed sequentially with water, aqueous sodium hydrogen carbonate solution, water, and saturated brine
  6. dry with materialThe solution was dried with magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe concentrated residue was separated
  9. custompurified by silica gel column chromatography (eluent: ethyl acetate/n-hexane =1/2)

Sources & evidence

ORD record
ord-a4809800c57d46ebb80f8296a43f9cee
Source dataset
uspto-grants-1990_04
Patent number
US04914097

Reaction notes

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