N,N-bis(3-aminopropyl)methylamine → HCID 67393258, compound

HRID 908664Notes

Reaction equation

HRID 908664 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]([CH3:10])[CH2:6][CH2:7][CH2:8][NH2:9].CO[C:13]1[C:21](=[O:22])[C:17]2[N:18]=[CH:19][S:20][C:16]=2[C:15](=[O:23])[CH:14]=1>C(O)C>[CH3:10][N:5]([CH2:6][CH2:7][CH2:8][NH:9][C:13]1[C:21](=[O:22])[C:17]2[N:18]=[CH:19][S:20][C:16]=2[C:15](=[O:23])[CH:14]=1)[CH2:4][CH2:3][CH2:2][NH:1][C:13]1[C:21](=[O:22])[C:17]2[N:18]=[CH:19][S:20][C:16]=2[C:15](=[O:23])[CH:14]=1

Participants

4

Reactant 2

HCID 7777N,N-bis(3-aminopropyl)methylamineHCID 67392986HCID 67392986, compound

Product 1

HCID 67393258HCID 67393258, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
85 °C

Procedure

57 μl (0.37 mmol; 0.48 equivalent) of N-(3-aminopropyl)-N-methylpropane-1,3-diamine is added to 150 mg (0.77 mmol) of 5-methoxy-1,3-benzothiazol-4,7-dione in solution in 6 ml of ethanol. The reaction mixture is maintained under stirring at 85° C. for 90 minutes, then the solvent is evaporated off under reduced pressure and the expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 94/6) and 95 mg (yield=26%) of 5.5′-[(methylimino)bis(propane-3,1-diylimino)]bis(1,3-benzothiazole-4,7-dione) is obtained in the form of a red powder. Melting point: 223-224° C.

Workup

  1. temperatureThe reaction mixture is maintained
  2. customthe solvent is evaporated off under reduced pressure
  3. customthe expected product is purified by chromatography on a silica column (eluent: dichloromethane/methanol mixture 94/6)

Sources & evidence

ORD record
ord-e578195f89ea483891ba5c1f12cba804
Source dataset
uspto-grants-2011_09
Patent number
US08017637B2

Reaction notes

Loading…