Dichloromethane → HCID 19768651, compound

HRID 1085835Notes

Reaction equation

HRID 1085835 reaction equation
[NH2:1][C:2]1[O: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[O: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 54176126HCID 54176126, compound

Product 1

HCID 19768651HCID 19768651, compoundYield 94%

Procedure

1.46 g (4.2 mmol) of t-butyl [2-(2-amino-5-phenyl-4-oxazolecarboxamido)ethyl]carbamate were dissolved in 50 ml of methylene chloride and treated with 5 ml of trifluoroacetic acid. The reaction mixture was heated to reflux while stirring for 2.5 hours and thereafter evaporated under reduced pressure. The residue was dissolved in methanol, treated with 5 ml of 2M methanolic hydrochloric acid and evaporated. Recrystallization of the residue from methanol/diethyl ether yielded 1.3 g (94%) of 2-amino-N-(2-aminoethyl)-5-phenyl-4-oxazolecarboxamide dihydrochloride as white crystals, melting point 260°.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux
  3. customevaporated under reduced pressure
  4. dissolutionThe residue was dissolved in methanol
  5. additiontreated with 5 ml of 2M methanolic hydrochloric acid
  6. customevaporated
  7. customRecrystallization of the residue from methanol/diethyl ether

Sources & evidence

ORD record
ord-4e60ea5f370440859d6985992399df7b
Source dataset
uspto-grants-1991_04
Patent number
US05011849

Reaction notes

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