Phosphorus sulfide (P2S5) → 2-(4-Pentyloxyphenyl)-5-(4-bromophenyl)thiazole

HRID 2270047Notes

Reaction equation

HRID 2270047 reaction equation
[CH2:1]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]([NH:13][CH2:14][C:15]([C:17]2[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=2)=O)=O)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:27].C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:6][C:7]1[CH:25]=[CH:24][C:10]([C:11]2[S:27][C:15]([C:17]3[CH:22]=[CH:21][C:20]([Br:23])=[CH:19][CH:18]=3)=[CH:14][N:13]=2)=[CH:9][CH:8]=1)[CH2:2][CH2:3][CH2:4][CH3:5]

Participants

5

Reactant 3

HCID 14817Phosphorus sulfide (P2S5)HCID 516892Sodium BicarbonateHCID 183310892-(4-Pentyloxybenzamido)-4'-bromoacetophenone

Product 1

HCID 183310882-(4-Pentyloxyphenyl)-5-(4-bromophenyl)thiazoleYield 105.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-pentyloxybenzamido)-4′-bromoacetophenone (3.39 g) in tetrahydrofuran (34 ml) was added phosphorus pentasulfide (2.43 g), and refluxed for 30 minutes. The reaction mixture was cooled, and poured into saturated sodium hydrogen carbonate aqueous solution (400 ml), and stirred for 1.5 hours. The resulting precipitate was collected by filtration to give 2-(4-pentyloxyphenyl)-5-(4-bromophenyl)thiazole (2.32 g).

Workup

  1. temperaturerefluxed for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-35db2723a2324f32b65e2a4e43386291
Source dataset
uspto-grants-2001_12
Patent number
US06331521B1

Reaction notes

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