2-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-one → 2-Acetylaminomethyl-4,5-bis(4-methoxyphenyl)thiazole

HRID 483976Notes

Reaction equation

HRID 483976 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[CH:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)Cl)=[CH:5][CH:4]=1.[C:21]([NH:24][CH2:25][C:26](=[S:28])[NH2:27])(=[O:23])[CH3:22]>C(O)C>[C:21]([NH:24][CH2:25][C:26]1[S:28][C:10]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:27]=1)(=[O:23])[CH3:22]

Participants

4

Reactant 2

HCID 38625232-Chloro-1,2-bis(4-methoxyphenyl)ethan-1-oneHCID 4435531N-(2-amino-2-thioxoethyl)acetamide

Product 1

HCID 100445402-Acetylaminomethyl-4,5-bis(4-methoxyphenyl)thiazoleYield 33.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1,2-bis(4-methoxyphenyl)-2-chloroethanone (5.99 g) and 2-(acetylamino)ethanethioamide (3.00 g) in ethanol (30 ml) was refluxed for 2 hours. After allowing to cool to room temperature, the solvent was evaporated in vacuo, and the residue was dissolved in chloroform (200 ml) and aqueous solution of sodium hydrogencarbonate (200 ml). The separated organic layer was washed with water and brine, dried over magnesium sulfate and treated with activated charcoal. After filtration, the filtrate was evaporated in vacuo. The resulting residue was dissolved in diethyl ether, added ethanol solution of hydrogen chloride, and the resulting precipitate was collected by filtration. The resulting crude compound was recrystallized with ethanol (10 ml). And the resulting crystal was collected by filtration, washed with ethanol and diethyl ether, and dried to give 2-acetylaminomethyl-4,5-bis(4-methoxyphenyl)thiazole (2.52 g).

Workup

  1. temperaturewas refluxed for 2 hours
  2. customthe solvent was evaporated in vacuo
  3. dissolutionthe residue was dissolved in chloroform (200 ml)
  4. washThe separated organic layer was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. additiontreated with activated charcoal
  7. filtrationAfter filtration
  8. customthe filtrate was evaporated in vacuo
  9. dissolutionThe resulting residue was dissolved in diethyl ether
  10. additionadded ethanol solution of hydrogen chloride
  11. filtrationthe resulting precipitate was collected by filtration
  12. customThe resulting crude compound was recrystallized with ethanol (10 ml)
  13. filtrationAnd the resulting crystal was collected by filtration
  14. washwashed with ethanol and diethyl ether
  15. customdried

Sources & evidence

ORD record
ord-1dadf65eb7cf4d2b92495264e5d079a6
Source dataset
uspto-grants-1993_07
Patent number
US05229386

Reaction notes

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