Acetic Acid → Methyl 6-cyanobenzo[b]thiophene-2-carboxylate

HRID 2179582

Reaction equation

HRID 2179582 reaction equation
[C:1]([C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[C:5]([N+]([O-])=O)[CH:4]=1)#[N:2].[SH:14][CH2:15][C:16]([O:18][CH3:19])=[O:17].C(N(CC)CC)C.C(O)(=O)C>CS(C)=O>[C:1]([C:3]1[CH:10]=[CH:9][C:6]2[CH:7]=[C:15]([C:16]([O:18][CH3:19])=[O:17])[S:14][C:5]=2[CH:4]=1)#[N:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 132385504-Formyl-3-nitrobenzonitrile

Product 1

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

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

4.08 g (23.2 mmol) of 4-cyano-2-nitrobenzaldehyde, 2.46 g (23.2 mmol) of methyl mercaptoacetate and 6.46 ml (46.4 mmol) of triethylamine are heated in 12.3 ml of DMSO at 80° C. for 2.5 h. The reaction solution is added to 400 ml of ice-water. The precipitate resulting after addition of 4 ml of acetic acid is filtered off with suction, washed twice with water and dried in vacuo at 50° C. overnight. 4.19 g (83.2% of theory) of the title compound are obtained.

Workup

  1. customThe precipitate resulting
  2. filtrationis filtered off with suction
  3. washwashed twice with water
  4. customdried in vacuo at 50° C. overnight

Sources & evidence

ORD record
ord-2942de0c9311436086102674b3ac815a
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Linked notes

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