2-Cyanoethanethioamide → HCID 54466438, compound

HRID 1378586Notes

Reaction equation

HRID 1378586 reaction equation
Br[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([CH3:21])(=O)=O)=[CH:14][CH:13]=1)[C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=1)=O.[C:22]([CH2:24][C:25]([NH2:27])=[S:26])#[N:23]>C(O)C>[C:22]([CH2:24][C:25]1[S:26][C:2]([C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:21])=[CH:14][CH:13]=2)=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([F:11])=[CH:7][CH:6]=2)[N:27]=1)#[N:23]

Participants

4

Reactant 2

HCID 14162772-CyanoethanethioamideHCID 112340792-Bromo-1-(4-fluorophenyl)-2-(4-(methylsulfonyl)phenyl)ethanone

Product 1

HCID 54466438HCID 54466438, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-bromo-1-(4-fluorophenyl)-2-(4-methylsulfonylphenyl)ethanone (Example 26, Step 2) (0.249 g, 0.734 mmol) in ethanol (9 mL) in a 25 mL round bottom flask was added 2-cyanothioacetamide (0.077 g, 0.771 mmol) and the solution heated to reflux for 14 hours. The reaction was cooled to room temperature, was was concentrated in vacuo and the residue dissolved in ethyl acetate. This solution was washed successively with Na2CO3 (10% solution) and brine, dried over Na2SO4, filtered and reconcentrated in vacuo yielding an orange crystalline solid. This solid was purified by flash chromatography (4:1 hexane:ethyl acetate ) yielding 2-(cyanomethyl)-4-(4-fluorophenyl)-5-(4-methylthiophenyl)thiazole as very fine pink crystals (0.090 g, 36%): mp 118°-119° C. 1H NMR (CDCl3) 400 mHz δ7.50 (d, J=5.38, 2H), 7.47 (d, J=5.38, 2H), 7.24-7.18 (m, 4H), 7.00 (t, J=8.80, 2H), 4.16 (s, 2H), 2.50 (s, 3H). MS (EI): m/z 340 (M+). HRMS Δ=2.7 mmu.

Workup

  1. temperaturethe solution heated
  2. temperatureto reflux for 14 hours
  3. concentrationwas was concentrated in vacuo
  4. dissolutionthe residue dissolved in ethyl acetate
  5. washThis solution was washed successively with Na2CO3 (10% solution) and brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customyielding an orange crystalline solid
  9. customThis solid was purified by flash chromatography (4:1 hexane:ethyl acetate )

Sources & evidence

ORD record
ord-ea63130d1e104280bf1d84d19c6b067e
Source dataset
uspto-grants-1997_09
Patent number
US05668161

Reaction notes

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