Hydrochloric Acid → N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine

HRID 447145Notes

Reaction equation

HRID 447145 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH2:12][NH:13]C(=O)OC(C)(C)C.Cl>O1CCOCC1>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][CH2:11][CH2:12][NH2:13]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 47453718Tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate

Product 1

HCID 61004338N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

tert-Butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate (515.7 mg, 1.86 mmol) was dissolved in warm p-dioxane (6 mL) and was treated with 4N HCl in 1,4-dioxane (6 mL, 24.0 mmol). The resulting mixture was stirred for 3 h as a solid separated from the acidic solution. Then, additional 4N HCl (2 mL, 8.0 mmol) was added and the resulting mixture stirred for 1 h, then stored in the freezer overnight. The resulting solid was collected by filtration, washed with 1,4-dioxane, then dried in vacuum oven overnight at room temperature to yield the corresponding hydrochloride salt of N1-(benzo[d]oxazol-2-yl)ethane-1,2-diamine as a white powder.

Workup

  1. customseparated from the acidic solution
  2. stirringthe resulting mixture stirred for 1 h
  3. customstored in the freezer overnight
  4. filtrationThe resulting solid was collected by filtration
  5. washwashed with 1,4-dioxane
  6. customdried in vacuum oven overnight at room temperature

Sources & evidence

ORD record
ord-b8845847c52a4a6c96c0e495917e2520
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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