Dimethyl Sulfoxide → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 1845124Notes

Reaction equation

HRID 1845124 reaction equation
F[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]=O)[C:5]#[N:6].CS(C)=O.C(N(CC)CC)C.[SH:23][CH2:24][C:25]([O:27][CH3:28])=[O:26]>O>[C:5]([C:4]1[CH:7]=[CH:8][C:9]2[CH:10]=[C:24]([C:25]([O:27][CH3:28])=[O:26])[S:23][C:2]=2[CH:3]=1)#[N:6]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 27831503-Fluoro-4-formylbenzonitrile

Product 1

HCID 11031280Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A round bottom flask was charged with 3-fluoro-4-formylbenzonitrile (9.00 g, 60.4 mmol), dimethyl sulfoxide (90 mL), triethylamine (18.0 mL, 129 mmol), and subsequently methyl 2-mercaptoacetate (5.40 mL, 60.4 mmol). The reaction mixture was heated at 80° C. for 2 hours. After cooling, the reaction mixture was poured into water and the precipitated product was collected by filtration, dried and used in the next step without further purification.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitated product was collected by filtration
  3. customdried
  4. customused in the next step without further purification

Sources & evidence

ORD record
ord-f035714f2b384703a09adaafccd42b7d
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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