2-Methoxybenzylamine → HCID 178489491, compound

HRID 1695578Notes

Reaction equation

HRID 1695578 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=1[N:19]=[C:20]=S)(C)C)(C)(C)C.[CH3:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][NH2:27].O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.CN(C)CCCN=C=NCC.CN(C)CCCNC(NCC)=S>C(#N)C.C(OCC)(=O)C.O>[CH3:22][O:23][C:24]1[CH:31]=[CH:30][CH:29]=[CH:28][C:25]=1[CH2:26][NH:27][C:20]1[O:8][CH2:9][C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[N:19]=1

Participants

9

Reactant 5

HCID 812922-MethoxybenzylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14633811N-[3-(Dimethylamino)propyl]-N'-ethylthioureaHCID 46855450tert-Butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane

Product 1

HCID 178489491HCID 178489491, compoundYield 76.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
23 °C

Procedure

To a stirred solution of tert-butyl-(2-isothiocyanato-5-nitro-benzyloxy)-dimethyl-silane (Example C1) (2.0 g, 6.0 mmol; HPLC: 4.446 min) in acetonitrile (30 mL) at 23° C. was added 2-methoxybenzylamine (0.82 ml, 6.0 mmol; HPLC: 1.773 min) and the mixture was stirred at 23° C. for 15 min (HPLC: 3.487 min 100%). Added tetrabutylammonium fluoride trihydrate (TBAF.3H2O) (1.945 g, 6.0 mmol) and stirred at 23° C. for 1 h (HPLC: 2.188 min 100%). Added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (1.772 g, 9.0 mmol) and stirred at 90° C. for 4 to 18 h (HPLC product at 1.667 min, 1-(3-dimethylamino-propyl)-3-ethyl-thiourea at 0.31 min). Cooled to rt, diluted with ethyl acetate and water, added little 1 M NaH2PO4.2H2O solution to achieve pH 4, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow foam, which was purified by flash chromatography on silica gel with n-heptane and ethyl acetate to give the title compound as a yellow foam (1.43 g, 74%), MS (ISP) m/e=288.8 [(M+H)+].

Workup

  1. temperatureCooled to rt
  2. customseparated phases
  3. washwashed organic layer with brine
  4. dry with materialdried over sodium sulfate
  5. customRemoval of the solvent in vacuum
  6. waitleft a yellow foam, which
  7. customwas purified by flash chromatography on silica gel with n-heptane and ethyl acetate

Sources & evidence

ORD record
ord-ceb735b351614b7fa2375ccdffff2bf7
Source dataset
uspto-grants-2012_04
Patent number
US08163740B2

Reaction notes

Loading…