Acetic Acid → HCID 58896500, compound

HRID 2235517Notes

Reaction equation

HRID 2235517 reaction equation
[C:1]1([CH3:21])[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][C:16]([CH3:20])=[CH:15][C:13]=2[N:14]=1.[CH:22](=O)[CH2:23][CH3:24].C(O[BH-](O[C:36](=O)[CH3:37])OC(=O)C)(=O)C.[Na+].[CH3:40]C(O)=O>ClCCl>[C:1]1([CH3:21])[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][CH2:36][CH3:37])[CH2:22][CH2:23][CH3:24])=[CH:17][C:16]([CH3:20])=[CH:15][C:13]=2[N:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 86049102HCID 86049102, compound

Product 1

HCID 58896500HCID 58896500, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N2-mesityl-5-methyl-1,3-benzothiazole-2,7-diamine (10 mg, 0.0336) in dichloromethane (1 ml) was added propionaldehyde (0.012 ml, 0.168 mmol) followed after 30 min by sodium triacetoxyborohydride (29 mg, 0.135 mmol) and AcOH (0.0039 ml). The mixture was stirred at room temperature for 18 h. The reaction was quenched with saturated NaHCO3 solution. The aqueous solution was extracted with dichloromethane. The extract was washed with brine, dried over magnesium sulfate and concentrated under vacuum. The residue was triturated with n-hexane. The resulting solid was collected by filtration to afford 6.8 mg of the title compound.

Workup

  1. customThe reaction was quenched with saturated NaHCO3 solution
  2. extractionThe aqueous solution was extracted with dichloromethane
  3. washThe extract was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under vacuum
  6. customThe residue was triturated with n-hexane
  7. filtrationThe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-08fbb4cec36844eea219537366be26bd
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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