Dichloromethane → N-(2-aminoethyl)-5-phenyl-4-thiazolecarboxamide hydrochloride
Reaction equation
[C:1]1([C:7]2[S:11][CH:10]=[N:9][C:8]=2[C:12]([NH:14][CH2:15][CH2:16][NH:17]C(=O)OC(C)(C)C)=[O:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:33]>>[ClH:33].[NH2:17][CH2:16][CH2:15][NH:14][C:12]([C:8]1[N:9]=[CH:10][S:11][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:13]Participants
4
Procedure
4.3 g (12.37 mmol) of t-butyl [2-(5-phenyl-4-thiazolecarboxamido)ethyl]carbamate were dissolved in 10 ml of methylene chloride, treated with 5.0 ml of trifluoro-acetic acid and stirred at 20° for 16 hours and at 60° for 1 hour. Subsequently, the mixture was concentrated under reduced pressure. The residue was dissolved in 10 ml of ethanol, treated with 3 ml of 17.5% (w/v) ethanolic hydro-chloric acid and evaporated. The residue was recrystallized from methanol, whereby 3.3 g (94%) of N-(2-aminoethyl)-5-phenyl-4-thiazolecarboxamide hydrochloride were obtained as white crystals, melting point 243°-245°.
Workup
- concentrationSubsequently, the mixture was concentrated under reduced pressure
- dissolutionThe residue was dissolved in 10 ml of ethanol
- additiontreated with 3 ml of 17.5% (w/v) ethanolic hydro-chloric acid
- customevaporated
- customThe residue was recrystallized from methanol
Sources & evidence
- ORD record
- ord-f832160ffcde4d529ca4fdf1f47b08da
- Source dataset
- uspto-grants-1991_04
- Patent number
- US05011849
Reaction notes
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