Benzoyl chloride → HCID 54432514, compound

HRID 2379825Notes

Reaction equation

HRID 2379825 reaction equation
[C:1](Cl)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[S-:10][C:11]#[N:12].[Na+].[NH2:14][C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH:27][C:28](=[O:31])[CH2:29][CH3:30])[N:21]=2)[N:19]=1>CC(C)=O>[C:1]([NH:12][C:11](=[S:10])[NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([CH2:26][NH:27][C:28](=[O:31])[CH2:29][CH3:30])[N:21]=2)[N:19]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 516871Sodium thiocyanateHCID 18956305HCID 18956305, compound

Product 1

HCID 54432514HCID 54432514, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl chloride (7.7 g) was added slowly to a solution of sodium thiocyanate (4.8 g) in acetone (220 ml) under refluxing and the mixture was refluxed for 15 minutes. 2-Amino-4-(6-propionylaminomethylpyridin-2-yl)thiazole (12.0 g) was added to the mixture. The mixture was refluxed for 4 hours. The resulting precipitate was collected by filtration and was washed with water and then acetone to afford 2-(3-benzoylthioureido)-4-(6-propionylaminomethylpyridin-2-yl)thiazole (16.5 g).

Workup

  1. temperatureunder refluxing
  2. temperaturethe mixture was refluxed for 15 minutes
  3. temperatureThe mixture was refluxed for 4 hours
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwas washed with water

Sources & evidence

ORD record
ord-9cee74f26c4342b8a57c94f6ac168b6b
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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