Ethanol → N-propyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine hydrobromide

HRID 2422251Notes

Reaction equation

HRID 2422251 reaction equation
[Br:1][CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=1)=O.[CH2:15]([NH:18][C:19]([NH2:21])=[S:20])[CH2:16][CH3:17].C(O)C>C(OC(C)C)(C)C>[BrH:1].[CH2:15]([NH:18][C:19]1[S:20][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][CH:6]=2)[N:21]=1)[CH2:16][CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 3219792-Bromo-4'-(trifluoromethyl)acetophenoneHCID 1615208Propyl-2-thiourea

Product 1

HCID 23082954N-propyl-4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-amine hydrobromideYield 70%

Reagents, catalysts & solvents 1

HCID 7914Diisopropyl EtherSolvent

Procedure

A mixture of 2-bromo-1-[4-(trifluoromethyl)phenyl]ethanone (5.34 g), N-propylthiourea (2.60 g) and ethanol (50 mL) was stirred for 1 hr while heating under reflux. The reaction mixture was cooled and diluted with isopropyl ether. The precipitated solid was collected by filtration, washed with isopropyl ether and dried to give the title compound (5.11 g, yield 70%) as colorless crystals.

Workup

  1. temperaturewhile heating
  2. temperatureunder reflux
  3. temperatureThe reaction mixture was cooled
  4. filtrationThe precipitated solid was collected by filtration
  5. washwashed with isopropyl ether
  6. customdried

Sources & evidence

ORD record
ord-be129a25c75a4a96a67dd0170d5191f1
Source dataset
uspto-grants-2011_06
Patent number
US07960369B2

Reaction notes

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