N,N-bis(3-aminopropyl)methylamine → 5.5'-[(Methylimino)bis(propane-3,1-diylimino)]bis(2-methyl-1,3-benzothiazole-4,7-dione)

HRID 908660Notes

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:22](=[O:23])[C:17]2[N:18]=[C:19]([CH3:21])[S:20][C:16]=2[C:15](=[O:24])[CH:14]=1>C(O)C>[CH3:10][N:5]([CH2:6][CH2:7][CH2:8][NH:9][C:13]1[C:22](=[O:23])[C:17]2[N:18]=[C:19]([CH3:21])[S:20][C:16]=2[C:15](=[O:24])[CH:14]=1)[CH2:4][CH2:3][CH2:2][NH:1][C:13]1[C:22](=[O:23])[C:17]2[N:18]=[C:19]([CH3:21])[S:20][C:16]=2[C:15](=[O:24])[CH:14]=1

Participants

Conditions

Temperature: 60 °C

Procedure

83.4 mg (0.57 mmol; 0.6 equivalents) of N-(3-aminopropyl)-N-methylpropane-1,3-diamine are added to 200 mg (0.95 mmol) of 5-methoxy-2-methyl-4,7-dioxobenzothiazole in solution in 15 ml of anhydrous ethanol. The reaction mixture is stirred at 60° C. for 2 hours, then the solvent is evaporated off under reduced pressure. The residue is purified on a silica column (eluent: methanol at 3% in dichloromethane) and 30 mg (yield=36%) of expected product is obtained in the form of a red powder. Melting point: 94-96° C.

Workup

customthe solvent is evaporated off under reduced pressure
customThe residue is purified on a silica column (eluent: methanol at 3% in dichloromethane)

Sources & evidence

ORD record: ord-b62cb25f10444310ac416c3dbada4d6b
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017637B2

Reaction notes

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