Diethylamine → Methyl 7-chlorobenzo[b]thiophene-2-carboxylate

HRID 507693Notes

Reaction equation

HRID 507693 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([CH:7]=[CH:8][CH:9]=1)[CH:5]=O.C[CH:12]([SH:16])[C:13]([O-:15])=[O:14].[CH2:17](NCC)C>CS(C)=O.O>[Cl:1][C:2]1[C:3]2[S:16][C:12]([C:13]([O:15][CH3:17])=[O:14])=[CH:5][C:4]=2[CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 3

HCID 8021DiethylamineHCID 7363353-Chloro-2-fluorobenzaldehydeHCID 156077362-Mercaptopropionate

Product 1

HCID 22474203Methyl 7-chlorobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

3-Chloro-2-fluorobenzaldehyde(1 g, 6.3 mmol) was dissolved in DMSO (10 mL) and treated with methylthioglycolate, followed by diethylamine (0.58 mL, 6.3 mmol). The reaction was heated to 70° C. and stirred overnight. The reaction was allowed to cool down to room temperature and diluted with water (25 mL). The solid that precipitated out of solution was collected by filtration and washed well with water. The solid was then purified by flash chromatography using a gradient of 2 to 20% ethyl acetate in hexanes to afford a white solid (0.8 g).

Workup

  1. temperatureto cool down to room temperature
  2. customThe solid that precipitated out of solution
  3. filtrationwas collected by filtration
  4. washwashed well with water
  5. customThe solid was then purified by flash chromatography

Sources & evidence

ORD record
ord-90ff0b1c32174bad8a060a0d7e9597a1
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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