Acetylthiourea → N-(4-{2-[4-(sulfanylmethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

HRID 1892537Notes

Reaction equation

HRID 1892537 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1.C(NC(N)=[S:25])(=O)C>C(O)C>[SH:25][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[N:12]=[C:13]([NH:16][C:17](=[O:19])[CH3:18])[S:14][CH:15]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 2723593AcetylthioureaHCID 21914927N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide

Product 1

HCID 86650043N-(4-{2-[4-(sulfanylmethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamideYield 86.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of N-(4-{2-[4-(chloromethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (589.7 mg, 2.000 mmol) in ethanol (10 ml) was added 1-acetyl-2-thiourea (472.6 mg, 4.000 mmol), and the mixture was heated under reflux for 19 hr. After cooling to room temperature, the mixture was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=2:3) to give N-(4-{2-[4-(sulfanylmethyl)phenyl]ethyl}-1,3-thiazol-2-yl)acetamide (507.7 mg, 1.736 mmol, yield 86.8%) as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 19 hr
  3. concentrationthe mixture was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 30 g, ethyl acetate:hexane=2:3)

Sources & evidence

ORD record
ord-3dc05467e23649b3b538e97022f1bf46
Source dataset
uspto-grants-2013_08
Patent number
US08507690B2

Reaction notes

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