Dichloromethane → HCID 19768594, compound

HRID 1085836Notes

Reaction equation

HRID 1085836 reaction equation
[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][CH2:10][CH2:11][NH:12]C(=O)OC(C)(C)C)=[O:8])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.FC(F)(F)C(O)=O.C(Cl)[Cl:34]>>[ClH:34].[NH2:1][C:2]1[O:6][N:5]=[C:4]([C:7]([NH:9][CH2:10][CH2:11][NH2:12])=[O:8])[C:3]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 53753211HCID 53753211, compound

Product 1

HCID 19768594HCID 19768594, compoundYield 73.5%

Procedure

1.5 g (4.33 mmol) of t-butyl [2-(5-amino-4-phenyl-3-isoxazolecarboxamido)ethyl]carbamate in 5 ml of methylene chloride were stirred at room temperature for 16 hours with 1.7 ml of trifluoroacetic acid. Thereafter, the reaction mixture was evaporated under reduced pressure: the residue was dissolved in ethanol, whereupon the solution was treated with 2 ml of ethanolic hydrochloric acid (17.5% w/v) and again evaporated. Recrystallization of the residue from methanol/ether yielded 0.9 g (73.5%) of 5-amino-N-(2-aminoethyl)-4-phenyl-3-isoxazolecarboxamide hydrochloride as white crystals, melting point 187°-189°.

Workup

  1. customThereafter, the reaction mixture was evaporated under reduced pressure
  2. dissolutionthe residue was dissolved in ethanol, whereupon the solution
  3. additionwas treated with 2 ml of ethanolic hydrochloric acid (17.5% w/v)
  4. customagain evaporated
  5. customRecrystallization of the residue from methanol/ether

Sources & evidence

ORD record
ord-308845ddf5d7445e84524103ca667231
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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