Diisopropylethylamine → HCID 60207429, compound

HRID 1192208Notes

Reaction equation

HRID 1192208 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1[S:8]([CH3:11])(=O)=O)#[N:2].[Na].[Cl:18][C:19]1[CH:20]=[N+:21]([O-])[CH:22]=[C:23]([Cl:26])C=1S.C(N(C(C)C)C(C)C)C>C(O)(C)C.CO>[C:1]([C:3]1[CH:4]=[C:5]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[S:6][C:7]=1[S:8][C:11]1[C:19]([Cl:18])=[CH:20][N:21]=[CH:22][C:23]=1[Cl:26])#[N:2]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 57848848HCID 57848848, compoundHCID 178507103HCID 178507103, compound

Product 1

HCID 60207429HCID 60207429, compoundYield 50.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3776IsopropanolSolvent

Procedure

To a 5 mL Biotage microwave reaction vessel was charged with a solution of Ethyl 4-cyano-5-(methylsulfonyl)thiophene-2-carboxylate (0.26 g, 1 mmol) in isopropanol (1.5 mL), 3,5-dichloro-1-oxido-pyridin-1-ium-4-thiol sodium salt (0.2 g, 1 mmol) and N-ethyl-N-isopropyl-propan-2-amine (0.645 g, 5.0 mmol). The resulting reaction mixture was sealed and heated at 150° C. for 10 minutes under microwave irradiation (Biotage Initiator 8). After cooling down, a precipitation was formed and the solid was removed by filtration. The organic solution was concentrated under vacuo to give a brown oil residue. The residue was re-dissolved in methanol (3 mL) and extracted with hexane (15 mL×4). The organic layer was separated and concentrated under vacuum to afford a solid as the title product (180 mg, 50% yield). MS m/z: 358.94, 360.94 [M+H]+.

Workup

  1. customTo a 5 mL Biotage microwave reaction vessel
  2. customThe resulting reaction mixture
  3. customwas sealed
  4. temperatureAfter cooling down
  5. customa precipitation
  6. customwas formed
  7. customthe solid was removed by filtration
  8. concentrationThe organic solution was concentrated under vacuo
  9. customto give a brown oil residue
  10. extractionextracted with hexane (15 mL×4)
  11. customThe organic layer was separated
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-5609e9cae1b3498c98ed9901974cd152
Source dataset
uspto-grants-2014_03
Patent number
US08680139B2

Reaction notes

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