N-BOC-ethylenediamine → HCID 47453722, compound

HRID 447141Notes

Reaction equation

HRID 447141 reaction equation
Br[C:2]1[S: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>[S: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 187201N-BOC-ethylenediamineHCID 6120402-Bromo-1,3-benzothiazole

Product 1

HCID 47453722HCID 47453722, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Bromo-1,3-benzothiazole (505.5 mg, 2.36 mmol) and N-(2-aminoethyl) carbamic acid tert-butyl ester (1.1356 g, 7.10 mmol) were stirred in a preheated oil bath (125° C.) for 5 h. The solid mass was dissolved in chloroform, and the resulting solution was washed with aqueous sodium bicarbonate then dried, filtered and concentrated to a yield a residue. The residue was purified by flash chromatography, eluting with 60% ethyl acetate in hexane to yield tert-butyl 2-(benzo[d]thiazol-2-ylamino)ethylcarbamate as a white amorphous solid.

Workup

  1. washthe resulting solution was washed with aqueous sodium bicarbonate
  2. customthen dried
  3. filtrationfiltered
  4. concentrationconcentrated to
  5. customa yield a residue
  6. customThe residue was purified by flash chromatography
  7. washeluting with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-a59e004208434ca18bb61e3d76927606
Source dataset
uspto-grants-2013_07
Patent number
US08481547B2

Reaction notes

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