Propanal → HCID 58896519, compound

HRID 2235485Notes

Reaction equation

HRID 2235485 reaction equation
[C:1]1([CH3:20])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([NH2:19])=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1.[CH:21](=O)[CH2:22][CH3:23].C(O[BH-](O[C:35](=O)[CH3:36])OC(=O)C)(=O)C.[Na+].Cl[CH:40](Cl)C>C(O)(=O)C>[C:1]1([CH3:20])[CH:6]=[C:5]([CH3:7])[CH:4]=[C:3]([CH3:8])[C:2]=1[NH:9][C:10]1[S:11][C:12]2[C:18]([N:19]([CH2:40][CH2:35][CH3:36])[CH2:21][CH2:22][CH3:23])=[CH:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 527PropanalHCID 63651,1-DichloroethaneHCID 5049666Sodium triacetoxyborohydrideHCID 86049183HCID 86049183, compound

Product 1

HCID 58896519HCID 58896519, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidCatalyst

Conditions

Temperature
50 °C

Procedure

To 0.125 g (0.44 mmol) of N2-mesityl-1,3-benzothiazole-2,7-diamine and 0.16 mL (2.2 mmol) of propionaldehyde in 5 mL of dichloroethane was added one drop of glacial acetic acid and 0.28 g (1.3 mmol) of sodium triacetoxyborohydride. The mixture was heated to 50° C. for 1 h and concentrated in vacuo. The crude solid was purified by flash chromatography eluting with a 2% methanol/dichloromethane mixture to give 0.016 g (10%) of the title compound as a tan powder.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe crude solid was purified by flash chromatography
  3. washeluting with a 2% methanol/dichloromethane mixture

Sources & evidence

ORD record
ord-41b1e331a1db424e8fe9457a1ceaaad7
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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