2-bromo-1-(4-methoxyphenyl)propan-1-one → 4-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminato

HRID 556087Notes

Reaction equation

HRID 556087 reaction equation
Br[CH:2]([CH3:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[NH2:14][C:15]([NH2:17])=[S:16].C([O-])(=O)C.[Na+]>>[CH3:12][O:11][C:8]1[CH:9]=[CH:10][C:5]([C:3]2[N:14]=[C:15]([NH2:17])[S:16][C:2]=2[CH3:13])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 2991022-bromo-1-(4-methoxyphenyl)propan-1-oneHCID 517045Sodium AcetateHCID 2723790Thiourea

Product 1

HCID 6132284-(4-Methoxyphenyl)-5-methyl-1,3-thiazol-2(3H)-iminatoYield 66.8%

Procedure

A procedure similar to step 5 of Example 6 was used. 2-bromo-1-(4-methoxy-phenyl)-propan-1-one prepared in the step 3, thiourea and anhydrous sodium acetate were used as starting materials, refluxed for 4 hours, followed by post-treatment to give a crude product, which was recrystallized with anhydrous ethanol to obtain a product as a white solid in a yield of 66.8%, mp: 139-140 └. 1H-NMR (CDCl3, 400 MHz) δ: 2.37 (3H, s, ArCH3), 3.84 (3H, s, OCH3), 5.09 (2H, br, NH2), 6.93 (2H, d, J=8.68 Hz, ArH), 7.50 (2H, d, J=8.68 Hz, ArH); EI-MS m/e (%): 220.1 (M+, 100), 205.1 (18), 163.1 (31); HREI-MS Calcd. for C11H12N2OS: 220.0670. found: 220.0672. Anal. Calcd. for C11H12N2OS: C, 59.98; H, 5.49; N, 12.72. found: C, 59.90; H, 5.52; N, 12.55.

Workup

  1. temperaturerefluxed for 4 hours
  2. customto give a crude product, which
  3. customwas recrystallized with anhydrous ethanol

Sources & evidence

ORD record
ord-b429078dd1ca46cd83f81b45fb89169d
Source dataset
uspto-grants-2011_11
Patent number
US08053581B2

Reaction notes

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