Propanal → N2-(1-Phenylethyl)-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamine

HRID 2235493Notes

Reaction equation

HRID 2235493 reaction equation
[C:1]1([CH:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:20](=O)[CH2:21][CH3:22].C(O[BH-](O[C:34](=O)[CH3:35])OC(=O)C)(=O)C.[Na+].Cl[CH:39](Cl)C>C(O)(=O)C>[C:1]1([CH:7]([NH:9][C:10]2[S:11][C:12]3[C:18]([N:19]([CH2:39][CH2:34][CH3:35])[CH2:20][CH2:21][CH3:22])=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 58896511N2-(1-Phenylethyl)-1,3-benzothiazole-2,7-diamine

Product 1

HCID 58896540N2-(1-Phenylethyl)-N7,N7-dipropyl-1,3-benzothiazole-2,7-diamineYield 38%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
50 °C

Procedure

To 0.016 g (0.059 mmol) of N2-(1-phenylethyl)-1,3-benzothiazole-2,7-diamine and 21 μL (0.30 mmol) of propionaldehyde in 2 mL of dichloroethane was added one drop of glacial acetic acid and 0.038 g (0.18 mmol) of sodium triacetoxyborohydride. The mixture was heated to 50° C. for 3 h and concentrated in vacuo. The crude solid was purified by flash chromatography eluting with a 25% ethyl acetate/hexanes mixture to give 0.008 g (38%) of the title compound as a light golden colored oil.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solid was purified by flash chromatography
  3. washeluting with a 25% ethyl acetate/hexanes mixture

Sources & evidence

ORD record
ord-f08fb6d0cffa41088c47faedf6307e87
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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