Ethanol → 2-(3'-Nitrophenyl)-4[(3'-methoxy)phenyl]thiazole

HRID 651390Notes

Reaction equation

HRID 651390 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10](=[S:12])[NH2:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[CH2:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.C[CH2:24][OH:25]>>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[S:12][CH:14]=[C:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([O:25][CH3:24])[CH:18]=3)[N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 6259Phenacyl bromideHCID 126681823-Nitrobenzene-1-carbothioamide

Product 1

HCID 226110652-(3'-Nitrophenyl)-4[(3'-methoxy)phenyl]thiazole

Procedure

A mixture of 3-nitrobenzenethioamide (2.73 g, 15 mmol) and 3-methoxy-α-[bromoacetophenone (3.43 g, 15 mmol) in EtOH (30 mL) is heated under reflux for 18 h. It is cooled and filtered to give 4 g of 2-(3′-nitrophenyl)-4[(3′-methoxy)phenyl]thiazole as a yellow solid, mp. 122-123° C. 1H NMR (CDCl3): δ 3.94 (s, 3 H), 6.90-7.01 (dd, 1 H), 7.32-7.48 (t, 1 H), 7.50-7.75 (m, 4 H), 8.22-8.45 (dd,dd 2 H), 8.90 (dd, 1 H),

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 18 h
  3. temperatureIt is cooled
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b4cdee07b3c94b8abbef18751b9c7fde
Source dataset
uspto-grants-2001_08
Patent number
US06281217B1

Reaction notes

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