Benzoyl chloride → HCID 10692374, compound

HRID 1033043Notes

Reaction equation

HRID 1033043 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[O:23][C:22]([C:24]2[N:25]=[C:26]([NH2:29])[S:27][CH:28]=2)=[CH:21][CH:20]=1)(=[O:16])[CH3:15]>CC(C)=O>[C:14]([NH:17][CH2:18][C:19]1[O:23][C:22]([C:24]2[N:25]=[C:26]([NH:29][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:27][CH:28]=2)=[CH:21][CH:20]=1)(=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 15666Ammonium thiocyanateHCID 7064095150208-26-7

Product 1

HCID 10692374HCID 10692374, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Benzoyl chloride (2.67 ml) was dropped to a refluxing solution of ammonium thiocyanate (1.92 g) in acetone (50 ml) and the mixture was refluxed for 15 minutes. 4-(5-Acetylaminomethylfuran-2-yl)-2-aminothiazole (5.20 g) was added portionwise to the refluxing mixture. After the mixture was refluxed for further two hours, the solvent was evaporated in vacuo and the residue was mixed with water and ethyl acetate. The resulting precipitate was collected by filtration and washed with ethyl acetate to afford 4-(5-acetylaminomethylfuran-2-yl)-2-(3-benzoylthioureido)thiazole (5.50 g).

Workup

  1. temperaturethe mixture was refluxed for 15 minutes
  2. temperatureAfter the mixture was refluxed for further two hours
  3. customthe solvent was evaporated in vacuo
  4. additionthe residue was mixed with water and ethyl acetate
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-0116f2f87fcd4d84a341fdcc19af44b4
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

Loading…