Isopropanol → 2-(4-Bromophenyl)-4-(4-(heptyloxy)phenyl)thiazole

HRID 1775815Notes

Reaction equation

HRID 1775815 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=1)=O.[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](=[S:26])[NH2:25])=[CH:22][CH:21]=1.C(O)(C)C>CCO>[Br:19][C:20]1[CH:28]=[CH:27][C:23]([C:24]2[S:26][CH:2]=[C:3]([C:5]3[CH:10]=[CH:9][C:8]([O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:7][CH:6]=3)[N:25]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 15492894-BromothiobenzamideHCID 539091862-Bromo-1-(4-(heptyloxy)phenyl)ethanone

Product 1

HCID 866896652-(4-Bromophenyl)-4-(4-(heptyloxy)phenyl)thiazoleYield 52%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirring solution of 2-bromo-1-(4-(heptyloxy)phenyl)ethanone INT-4 (1.37 g, 4.38 mmol) in EtOH (10 mL) were added 4-bromobenzothioamide (0.95 g, 4.38 mmol) and isopropanol (10 mL). The reaction mixture was stirred at room temperature for 16 h. The solid was isolated by filtration, washed with EtOH (5 mL) then taken up in DCM (10 mL) and NaHCO3 (20 mL) and stirred for 1 h at room temperature. The solid was isolated by filtration, washed with water (2×10 mL) and acetonitrile (2×4 mL) then dried to afford 1.02 g (52%) of 2-(4-bromophenyl)-4-(4-(heptyloxy)phenyl)thiazole as a white micro-crystalline solid. LCMS-ESI (m/z) calculated for C22H24BrNOS: 429.1. found 430.0 [M+H]+, tR=3.20 min. (Method 4).

Workup

  1. customThe solid was isolated by filtration
  2. washwashed with EtOH (5 mL)
  3. stirringNaHCO3 (20 mL) and stirred for 1 h at room temperature
  4. customThe solid was isolated by filtration
  5. washwashed with water (2×10 mL) and acetonitrile (2×4 mL)
  6. customthen dried

Sources & evidence

ORD record
ord-79da9b4c11fd43f0a3b8e949bb7c072d
Source dataset
uspto-grants-2016_02
Patent number
US09260427B2

Reaction notes

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