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

HRID 716399Notes

Reaction equation

HRID 716399 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 RT 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 RT. 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 RT
  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-4945f5d423bb4112b1b96ff1595d5e0f
Source dataset
uspto-grants-2015_11
Patent number
US09187522B2

Reaction notes

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