Iodine → 2-Amino-4-Phenylthiazole-5-carbonitrile

HRID 880602Notes

Reaction equation

HRID 880602 reaction equation
[C:1]([CH2:9][C:10]#[N:11])(=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[NH2:18][C:19]([NH2:21])=[S:20].II.[O-]S([O-])(=S)=O.[Na+].[Na+]>CCO>[NH2:21][C:19]1[S:20][C:9]([C:10]#[N:11])=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:18]=1

Participants

7

Reactant 5

HCID 807IodineHCID 1049PyridineHCID 24477Sodium ThiosulfateHCID 64799BenzoylacetonitrileHCID 2723790Thiourea

Product 1

HCID 214555522-Amino-4-Phenylthiazole-5-carbonitrile

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a solution of benzoylacetonitrile derivative (1 eq.) in EtOH is added pyridine (1 eq.). The resulting mixture is stirred at 70° C. for 15 min then cooled at r.t. A previously stirred suspension of thiourea (2 eq.) and iodine (1 eq.) in EtOH is then slowly added. After 1 h at r.t. a cold 1M Na2S2O3 solution is added under stirring. The resulting precipitate is filtered, washed with water, and finally dried under vacuo to afford the amino-4-phenyl-thiazole-5-carbonitrile derivative.

Workup

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

Sources & evidence

ORD record
ord-20d2e55bd4f34759bd8392d88d2dd222
Source dataset
uspto-grants-2015_03
Patent number
US08993590B2

Reaction notes

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