Trifluoroacetic acid → N-(2-aminoethyl)-2-bromo-5-phenyl-4-thiazolecarboxamide hydrobromide

HRID 1085832Notes

Reaction equation

HRID 1085832 reaction equation
[Br:1][C:2]1[S:3][C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[C:5]([C:7]([NH:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[O:8])[N:6]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[BrH:1].[NH2:12][CH2:11][CH2:10][NH:9][C:7]([C:5]1[N:6]=[C:2]([Br:1])[S:3][C:4]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:8]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 54063106t-Butyl [2-(2-bromo-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate

Product 1

HCID 19768792N-(2-aminoethyl)-2-bromo-5-phenyl-4-thiazolecarboxamide hydrobromideYield 184.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.5 g (1.2 mmol) of t-butyl [2-(2-bromo-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate, 2 ml of trifluoroacetic acid and 10 ml of methylene chloride were heated to reflux for 2 hours and then evaporated. The residue was dissolved in methanol and treated with 1 ml of hydrobromic acid in glacial acetic acid (- 30%). Renewed evaporation and recrystallization of the residue from methanol/ether yields 0.45 g (94.2%) of N-(2-aminoethyl)-2-bromo-5-phenyl-4-thiazolecarboxamide hydrobromide as beige crystals, melting point 214°-215° (dec.).

Workup

  1. temperatureto reflux for 2 hours
  2. customevaporated
  3. dissolutionThe residue was dissolved in methanol
  4. additiontreated with 1 ml of hydrobromic acid in glacial acetic acid (- 30%)
  5. customRenewed evaporation and recrystallization of the residue from methanol/ether

Sources & evidence

ORD record
ord-8b67beac9a534393ac4665701a8cc2dd
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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