Iodine → HCID 83535263, compound

HRID 880603Notes

Reaction equation

HRID 880603 reaction equation
[F:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([CH2:8][C:9]#[N:10])=O)=[CH:4][CH:3]=1.N1C=CC=CC=1.[NH2:19][C:20]([NH2:22])=[S:21].II.[O-]S([O-])(=S)=O.[Na+].[Na+]>CCO>[NH2:22][C:20]1[S:21][C:8]([C:9]#[N:10])=[C:6]([C:5]2[CH:11]=[CH:12][C:2]([F:1])=[CH:3][CH:4]=2)[N:19]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1049PyridineHCID 24477Sodium ThiosulfateHCID 2723790ThioureaHCID 2783172p-Fluorobenzoylacetonitrile

Product 1

HCID 83535263HCID 83535263, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of 4-fluorobenzoylacetonitrile (50 g, 306 mmol, 1 eq.) in EtOH (600 mL) was added pyridine (24.7 mL, 306 mmol, 1 eq.). The resulting mixture was stirred at 70° C. for 15 min then cooled to r.t. A previously stirred suspension of thiourea (46.7 g, 613 mmol, 2 eq.) and iodine (77.8 g, 306 mmol, 1 eq.) in EtOH (300 mL) was then slowly added. After 1 h at r.t. a cold 1 M Na2S2O3 solution (360 mL) was added under stirring. The resulting precipitate was filtered, washed with water, and finally dried under vacuo to afford 2-Amino-4-(4-fluoro-phenyl)-thiazole-5-carbonitrile.

Workup

  1. temperaturethen cooled to r.t
  2. additionwas then slowly added
  3. stirringunder stirring
  4. filtrationThe resulting precipitate was filtered
  5. washwashed with water
  6. customfinally dried under vacuo

Sources & evidence

ORD record
ord-fd0776f05a314625929195c8ff0adb2d
Source dataset
uspto-grants-2015_03
Patent number
US08993590B2

Reaction notes

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