Water → 4-(2-Amino-1,3-thiazol-4-yl)benzonitrile

HRID 1436463Notes

Reaction equation

HRID 1436463 reaction equation
[NH2:1][C:2]([NH2:4])=[S:3].[C:5]([C:7]1[CH:16]=[CH:15][C:10]([C:11](=O)[CH2:12]Br)=[CH:9][CH:8]=1)#[N:6].[OH-].[Na+].O>C(O)C>[NH2:1][C:2]1[S:3][CH:12]=[C:11]([C:10]2[CH:15]=[CH:16][C:7]([C:5]#[N:6])=[CH:8][CH:9]=2)[N:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 986544-(Bromoacetyl)benzonitrileHCID 2723790Thiourea

Product 1

HCID 20495894-(2-Amino-1,3-thiazol-4-yl)benzonitrileYield 90%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Thiourea (0.76 g, 10 mmol) was added to 4-cyanophenacyl bromide (2.0 g, 8.9 mmol) in ethanol (20 mL), and the reaction heated under reflux. After 45 min, the mixture was cooled to room temperature, and poured into 2N NaOH (10 mL)/water (40 mL). The precipitate was collected and air-dried to give 4-(2-amino-thiazol-4-yl)benzonitrile (1.6 g, 90%), which was used without further characterization.

Workup

  1. temperaturethe reaction heated
  2. temperatureunder reflux
  3. customThe precipitate was collected
  4. customair-dried

Sources & evidence

ORD record
ord-f829c169ee5646be8d2dcd12e1074985
Source dataset
uspto-grants-2009_11
Patent number
US07618990B2

Reaction notes

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