Dimethylformamide → 2-(2-Ethynyl-4-fluorophenyl)acetyl isothiocyanate

HRID 1711089Notes

Reaction equation

HRID 1711089 reaction equation
[C:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH2:10][C:11]([OH:13])=O)#[CH:2].C(Cl)(=O)C(Cl)=O.CN(C=O)C.[Pb](SC#N)[S:26][C:27]#[N:28]>ClCCl>[C:1]([C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH2:10][C:11]([N:28]=[C:27]=[S:26])=[O:13])#[CH:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 516874BleirhodanidHCID 594577442-(2-Ethynyl-4-fluorophenyl)acetic acid

Product 1

HCID 594577012-(2-Ethynyl-4-fluorophenyl)acetyl isothiocyanate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of acid 327 (2.10 g, 11.8 mmol) in dry dichloromethane (50 mL) was added oxalyl chloride (2.0 mL, 2.9 g, 23 mmol) and dry DMF (0.1 mL). The mixture was stirred for 1 h, then concentrated under reduced pressure. The residue was re-dissolved in toluene (75 mL) and lead thiocyanate (4.0 g, 12 mmol) was added. The resulting suspension was heated to reflux with vigorous stirring for 3 h, then cooled, filtered through celite, and concentrated to afford crude 321 which was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was re-dissolved in toluene (75 mL)
  3. temperatureThe resulting suspension was heated
  4. temperatureto reflux
  5. stirringwith vigorous stirring for 3 h
  6. temperaturecooled
  7. filtrationfiltered through celite
  8. concentrationconcentrated
  9. customto afford crude 321 which
  10. customwas used without further purification

Sources & evidence

ORD record
ord-82d78576a1e64465b4d64901352e228b
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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