Benzoyl chloride → HCID 11133382, compound

HRID 2379808Notes

Reaction equation

HRID 2379808 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].[NH4+].[C:14]([NH:17][CH2:18][C:19]1[N:24]=[C:23]([C:25]2[N:26]=[C:27]([NH2:30])[S:28][CH:29]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:16])[CH3:15]>CC(C)=O>[C:14]([NH:17][CH2:18][C:19]1[N:24]=[C:23]([C:25]2[N:26]=[C:27]([NH:30][C:11]([NH:12][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:10])[S:28][CH:29]=2)[CH:22]=[CH:21][CH:20]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 10944783HCID 10944783, compound

Product 1

HCID 11133382HCID 11133382, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl chloride (15.7 ml) was dropped to a refluxing solution of ammonium thiocyanate (11.3 g) in acetone (640 ml) and the mixture was refluxed for 20 minutes. 4-(6-Acetylaminomethylpyridin-2-yl)-2-aminothiazole (32.0 g) was added portionwise to the refluxing mixture. After the mixture was refluxed for 3 hours, the solvent was evaporated in vacuo and the residue was mixed with ethyl acetate, tetrahydrofuran and water. The mixture was adjusted to pH 9.5 with 20% aqueous potassium carbonate and resulting precipitate was collected by filtration to give 4-(6-acetylaminomethylpyridin-2-yl)-2-(3-benzoylthioureido)thiazole (15.11 g).

Workup

  1. temperaturethe mixture was refluxed for 20 minutes
  2. temperatureAfter the mixture was refluxed for 3 hours
  3. customthe solvent was evaporated in vacuo
  4. additionthe residue was mixed with ethyl acetate, tetrahydrofuran and water
  5. customresulting precipitate
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-f0096e6946d64193b5e962ae0019c648
Source dataset
uspto-grants-1994_11
Patent number
US05364871

Reaction notes

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