5-Methoxy-2-methylbenzo[d]thiazole-4,7-dione → 5.5'-[(Methylimino)bis(butane-4,1-diylimino)]bis(2-methyl-1,3-benzothiazole-4,7-dione)

HRID 908678Notes

Reaction equation

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][N:6]([CH3:12])[CH2:7][CH2:8][CH2:9][CH2:10][NH2:11].CO[C:15]1[C:24](=[O:25])[C:19]2[N:20]=[C:21]([CH3:23])[S:22][C:18]=2[C:17](=[O:26])[CH:16]=1>C(O)C>[CH3:12][N:6]([CH2:5][CH2:4][CH2:3][CH2:2][NH:1][C:15]1[C:24](=[O:25])[C:19]2[N:20]=[C:21]([CH3:23])[S:22][C:18]=2[C:17](=[O:26])[CH:16]=1)[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:15]1[C:24](=[O:25])[C:19]2[N:20]=[C:21]([CH3:23])[S:22][C:18]=2[C:17](=[O:26])[CH:16]=1

Participants

Conditions

Temperature: 60 °C

Procedure

6 mg (34 μmol) of N-(4-aminobutyl)-N-methylbutane-1,4-diamine is added to a solution of 15 mg (71 mmol; 2.1 equivalents) of 5-methoxy-2-methyl-1,3-benzothiazole-4,7-dione in 1.5 ml of ethanol, then the reaction mixture is stirred at 60° C. for 1 hour. The solvent is then evaporated off under reduced pressure and the expected product is obtained by purification by chromatography on a silica column (eluent: dichloromethane/methanol: 95/5) in the form of a red oil.

Workup

customThe solvent is then evaporated off under reduced pressure

Sources & evidence

ORD record: ord-8601122550904434adfe852947592747
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08017637B2

Reaction notes

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