Propanal → N-(7-(Dipropylamino)-1,3-benzothiazol-2-yl)-2,4,6-trimethylbenzamide

HRID 2235501Notes

Reaction equation

[NH2:1][C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:22])[C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.[CH:23](=O)[CH2:24][CH3:25].C(O[BH-](O[C:37](=O)[CH3:38])OC(=O)C)(=O)C.[Na+].Cl[CH:42](Cl)C>C(O)(=O)C>[CH2:23]([N:1]([CH2:42][CH2:37][CH3:38])[C:2]1[C:10]2[S:9][C:8]([NH:11][C:12](=[O:22])[C:13]3[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=3[CH3:21])=[N:7][C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:24][CH3:25]

Participants

Conditions

Temperature: 50 °C

Procedure

To 0.118 g (0.379 mmol) of N-(7-amino-1,3-benzothiazol-2-yl)-2,4,6-trimethylbenzamide and 0.14 mL (1.9 mmol) of propionaldehyde in 5 mL of dichloroethane was added one drop of glacial acetic acid and 0.24 g (1.1 mmol) of sodium triacetoxyborohydride. The mixture was heated to 50° C. for 3 h and an additional 0.14 mL of propionaldehyde was added. The reaction was heated at 50° C. for 18 h and concentrated in vacuo. The crude solid was purified by flash chromatography eluting with a 13% ethyl acetate/hexanes mixture to give 0.080 g (53%) of the title compound as a cream colored powder.

Workup

temperatureThe reaction was heated at 50° C. for 18 h
concentrationconcentrated in vacuo
customThe crude solid was purified by flash chromatography
washeluting with a 13% ethyl acetate/hexanes mixture

Sources & evidence

ORD record: ord-812d0464773b40978e93705bfc957ee4
Source dataset: uspto-grants-2010_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07714009B2

Reaction notes

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