Trifluoroacetic acid → 5-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

HRID 871002Notes

Reaction equation

HRID 871002 reaction equation
[Cl:1][C:2]1[C:6]([C:7]#[N:8])=[C:5]([C:9]2[CH:14]=[CH:13][C:12]([NH:15]C(=O)OC(C)(C)C)=[CH:11][CH:10]=2)[S:4][N:3]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([C:5]2[S:4][N:3]=[C:2]([Cl:1])[C:6]=2[C:7]#[N:8])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86689222tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate

Product 1

HCID 866892235-(4-Aminophenyl)-3-chloroisothiazole-4-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of tert-Butyl 4-(3-chloro-4-cyanoisothiazol-5-yl)phenylcarbamate (4.76 g, 13.38 mmol) in DCM (100 ml) was treated with 10 mL of TFA. The reaction mixture was stirred at RT overnight. Solvent was removed in vacuo. The residue was diluted with water and DCM (100 ml). Layers were separated and the aqueous layer was extracted with DCM×2. The combined organics was washed with brine and dried with MgSO4, filtered, and concentrated. Product was rinsed with Et2O/hexanes and collected by filtration as a bright yellow solid (3.15 g, 94%).

Workup

  1. customSolvent was removed in vacuo
  2. additionThe residue was diluted with water and DCM (100 ml)
  3. customLayers were separated
  4. extractionthe aqueous layer was extracted with DCM×2
  5. washThe combined organics was washed with brine
  6. dry with materialdried with MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. washProduct was rinsed with Et2O/hexanes
  10. filtrationcollected by filtration as a bright yellow solid (3.15 g, 94%)

Sources & evidence

ORD record
ord-e139ca9805d64efcb72214d9a8de634b
Source dataset
uspto-grants-2015_03
Patent number
US08969583B2

Reaction notes

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