2-Chlorobenzoxazole → Tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate

HRID 447144Notes

Reaction equation

HRID 447144 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[C:11]([O:15][C:16](=[O:21])[NH:17][CH2:18][CH2:19][NH2:20])([CH3:14])([CH3:13])[CH3:12]>C(Cl)(Cl)Cl>[O:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH:20][CH2:19][CH2:18][NH:17][C:16](=[O:21])[O:15][C:11]([CH3:13])([CH3:12])[CH3:14]

Participants

4

Reactant 2

HCID 119862-ChlorobenzoxazoleHCID 187201N-BOC-ethylenediamine

Product 1

HCID 47453718Tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 2-chlorobenzoxazole (0.6 mL, 5.16 mmol) and N-(2-aminoethyl) carbamic acid tert-butyl ester (2.4328 g, 15.18 mmol)) was stirred in a preheated oil bath at 125° C. for 5 h, then held at room temperature overnight. The solidified mixture was dissolved in chloroform (125 mL), washed with aqueous sodium bicarbonate (2×150 mL), then brine (1×150). The organic layer was dried over sodium sulfate, then filtered and concentrated in vacuo. The resulting residue was purified by flash column chromatography, eluting with 60% ethyl acetate in heptane to yield tert-butyl 2-(benzo[d]oxazol-2-ylamino)ethylcarbamate as a beige powder.

Workup

  1. waitheld at room temperature overnight
  2. washwashed with aqueous sodium bicarbonate (2×150 mL)
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash column chromatography
  7. washeluting with 60% ethyl acetate in heptane

Sources & evidence

ORD record
ord-6c940d0472ba490c9940a6b75fb13a00
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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