Hydrochloric Acid → Benzo[b]thiophene-6-carbonitrile

HRID 1845126Notes

Reaction equation

HRID 1845126 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]2[CH:10]=[C:9](C(O)=O)[S:8][C:7]=2[CH:14]=1)#[N:2].N12CCCN=C1CCCCC2.Cl>CN(C)C(=O)C>[S:8]1[CH:9]=[CH:10][C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:14][C:7]1=2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 106796506-Cyanobenzo[b]thiophene-2-carboxylic acid

Product 1

HCID 21816574Benzo[b]thiophene-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

A microwave vial was charged with 6-cyanobenzo[b]thiophene-2-carboxylic acid (1.90 g, 9.35 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (5.6 mL, 37.4 mmol) and N,N-dimethylacetamide (15 mL) and the reaction was subjected to microwave irradiation at 190° C. for 1 hour. After cooling, the reaction mixture was poured into 1N aq. HCl and extracted with ethyl acetate. The organic phase was concentrated under reduced pressure to get the product as light brown solid.

Workup

  1. customirradiation at 190° C. for 1 hour
  2. temperatureAfter cooling
  3. extractionextracted with ethyl acetate
  4. concentrationThe organic phase was concentrated under reduced pressure

Sources & evidence

ORD record
ord-524232558f104bde85cd2a4ee03859a5
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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