4-Nitrobenzylamine → HCID 178454248, compound

HRID 1169384Notes

Reaction equation

HRID 1169384 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].CS[C:14](=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>C1COCC1>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:14]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:23][C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 291474-NitrobenzylamineHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 178454248HCID 178454248, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4-nitrobenzylamine (5.24 g, 34.4 mmol) and S-methyl-N,N′-bis(tert-butoxycarbonyl)isothiourea (5.00 g, 17.2 mmol) in THF (60 ml) was stirred at 55° C. for 9 hours and at room temperature for 11 hours. The reaction mixture was concentrated under reduced pressure, was then mixed with ethyl acetate (150 ml) and was washed with 1 N hydrochloric acid (30 ml×3) and an aqueous saturated solution of sodium chloride (30 ml) in the order. The organic layer was dried with anhydrous magnesium sulfate and was then concentrated under reduced pressure, and the residue was subjected to column chromatography (silica gel, 150 g: ethyl acetate/hexane 1/9→1/6). The objective fractions were concentrated under reduced pressure, diisopropyl ether was added to the residue and an insoluble material was collected by filtration. The insoluble material was washed with diisopropyl ether and was then dried under reduced pressure to obtain N-(4-nitrobenzyl)-N′,N″-bis(tert-butoxycarbonyl)guanidine (5.67 g, 14.4 mmol, 83%)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionwas then mixed with ethyl acetate (150 ml)
  3. washwas washed with 1 N hydrochloric acid (30 ml×3)
  4. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  5. concentrationwas then concentrated under reduced pressure
  6. concentrationThe objective fractions were concentrated under reduced pressure, diisopropyl ether
  7. additionwas added to the residue
  8. filtrationan insoluble material was collected by filtration
  9. washThe insoluble material was washed with diisopropyl ether
  10. customwas then dried under reduced pressure

Sources & evidence

ORD record
ord-818712e706924c3eb3f4f275695c9e36
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…