Dichloromethane → 2-amino-N-(2-aminoethyl)-5-phenyl-4-thiazolecarboxamide dihydrochloride

HRID 1590883Notes

Reaction equation

HRID 1590883 reaction equation
[NH2:1][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:34]>>[ClH:34].[ClH:34].[NH2:1][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][NH2:12])=[O:8])[N:6]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 54052891t-Butyl [2-(2-amino-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate

Product 1

HCID 197687322-amino-N-(2-aminoethyl)-5-phenyl-4-thiazolecarboxamide dihydrochlorideYield 90%

Procedure

2.0 g (5.5 mmol) of t-butyl [2-(2-amino-5-phenyl-4-thiazolecarboxamido)ethyl]carbamate were dissolved in 15 ml of methylene chloride and heated to reflux for 3 hours with 2.1 ml (27.6 mmol) of trifluoroacetic acid. Thereafter, the reaction mixture was evaporated under reduced pressure and the residue was dissolved in methanol, treated with ~2 M methanolic hydrochloric acid and evaporated. Recrystallization of the residue from methanol/ether with the addition of a small amount of hexane yielded 1.65 g (90%) of 2-amino-N-(2-aminoethyl)-5-phenyl-4-thiazolecarboxamide dihydrochloride as white crystals, melting point 203°14 205°.

Workup

  1. temperatureheated
  2. customThereafter, the reaction mixture was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in methanol
  4. additiontreated with ~2 M methanolic hydrochloric acid
  5. customevaporated
  6. customRecrystallization of the residue from methanol/ether
  7. additionwith the addition of a small amount of hexane

Sources & evidence

ORD record
ord-31e9156be8174352b8b899dc090e2c55
Source dataset
uspto-grants-1993_04
Patent number
US05204482

Reaction notes

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