Ethyl formate → HCID 59693390, compound

HRID 898880Notes

Reaction equation

HRID 898880 reaction equation
[NH2:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11][C:12](=[O:16])[N:13]([CH3:15])[CH3:14])[CH:8]=2)[CH2:3]1.[CH:17](OCC)=[O:18]>C(Cl)(Cl)Cl>[CH:17]([NH:1][CH:2]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:11][C:12](=[O:16])[N:13]([CH3:14])[CH3:15])[CH:8]=2)[CH2:3]1)=[O:18]

Participants

4

Reactant 2

HCID 8025Ethyl formateHCID 59693403HCID 59693403, compound

Product 1

HCID 59693390HCID 59693390, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
55 °C

Procedure

To dimethylthiocarbamic acid-S-[2-aminoindan-5-yl) ester (2.0 g; 8.46 mmol) in CHCl3 (10 mL) is added ethyl formate (50 mL) and the reaction heated at 55° C. for 24 h. The reaction is cooled, the solvent removed under reduced pressure, and the crude oil purified by flash chromatography (SiO2) eluting with an ethyl acetate-methanol gradient to afford 0.77 g (35%) of dimethylthiocarbamic acid-S-(2-formylaminoindan-5-yl)ester as a white solid.

Workup

  1. temperatureThe reaction is cooled
  2. customthe solvent removed under reduced pressure
  3. customthe crude oil purified by flash chromatography (SiO2)
  4. washeluting with an ethyl acetate-methanol gradient

Sources & evidence

ORD record
ord-1df23bd9a9a2426c8e15a17446e60bed
Source dataset
uspto-grants-2008_04
Patent number
US07351857B2

Reaction notes

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