2-Fluoro-4-(trifluoromethyl)phenylacetonitrile → 4-[5-Amino-4-(2-fluoro-4-trifluoromethyl-phenyl)-[1,2,3]triazol-1-yl]-benzenesulfonamide

HRID 1639691Notes

Reaction equation

HRID 1639691 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[CH:4][C:3]=1[CH2:12][C:13]#[N:14].[N:15]([C:18]1[CH:23]=[CH:22][C:21]([S:24]([NH2:27])(=[O:26])=[O:25])=[CH:20][CH:19]=1)=[N+:16]=[N-:17].C[O-].[Na+]>CO>[NH2:14][C:13]1[N:15]([C:18]2[CH:19]=[CH:20][C:21]([S:24]([NH2:27])(=[O:25])=[O:26])=[CH:22][CH:23]=2)[N:16]=[N:17][C:12]=1[C:3]1[CH:4]=[CH:5][C:6]([C:8]([F:10])([F:11])[F:9])=[CH:7][C:2]=1[F:1]

Participants

5

Reactant 3

HCID 27375972-Fluoro-4-(trifluoromethyl)phenylacetonitrileHCID 35585904-AzidobenzenesulfonamideHCID 10942334Sodium Methoxide

Product 1

HCID 252156754-[5-Amino-4-(2-fluoro-4-trifluoromethyl-phenyl)-[1,2,3]triazol-1-yl]-benzenesulfonamideYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and ice-cooled solution of 2-fluoro-4-(trifluoromethyl)phenyl acetonitrile (1.066 g, 5.2471 mmol) and 4-azido-benzenesulfonamide (0.800 g, 4.0362 mmol) in methanol (50 ml), sodium methoxide (0.3271 g, 6.0543 mmol) is added portion wise and the mixture is allowed to attain room temperature spontaneously and stirred for additional 24 hours at this temperature. The reaction mixture is concentrated, water (10 ml) is added and extracted with ethyl acetate (3×80 ml). The combined organic layers are washed with brine (15 ml), dried over MgSO4, filtered and concentrated to afford an off-white solid (1.61 g, ˜99% yield, 97.7% pure at HPLC). M.p. 183.8-185.2° C. LC-ESI-HRMS of [M+H]+ shows 402.0638 Da. Calc. 402.064783 Da, dev. −2.4 ppm.

Workup

  1. additionis added portion wise
  2. customto attain room temperature
  3. stirringstirred for additional 24 hours at this temperature
  4. concentrationThe reaction mixture is concentrated
  5. additionwater (10 ml) is added
  6. extractionextracted with ethyl acetate (3×80 ml)
  7. washThe combined organic layers are washed with brine (15 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford an off-white solid (1.61 g, ˜99% yield, 97.7% pure at HPLC)

Sources & evidence

ORD record
ord-c0cc5c3fcfaa45c38406f05b4193dd16
Source dataset
uspto-grants-2012_02
Patent number
US08110588B2

Reaction notes

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