Acetic Acid → 2-(2,4-Dimethylphenoxy)-N,N-dipropyl-1,3-benzothiazol-7-amine

HRID 2235505Notes

Reaction equation

HRID 2235505 reaction equation
[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[S:6][C:7]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1.[CH:20](=O)[CH2:21][CH3:22].C(O[BH-](O[C:34](=O)[CH3:35])OC(=O)C)(=O)C.[Na+].[CH3:38]C(O)=O>ClCCl>[CH3:1][C:2]1[CH:18]=[C:17]([CH3:19])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[S:6][C:7]2[C:13]([N:14]([CH2:38][CH2:34][CH3:35])[CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=[CH:10][C:8]=2[N:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 527PropanalHCID 5049666Sodium triacetoxyborohydrideHCID 685813992-(2,4-Dimethylphenoxy)-1,3-benzothiazol-7-amine

Product 1

HCID 588965172-(2,4-Dimethylphenoxy)-N,N-dipropyl-1,3-benzothiazol-7-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(2,4-dimethylphenoxy)-1,3-benzothiazol-7-amine (54 mg, 0.200 mmol) in dichloromethane (DCM) (3 ml) was added propionaldehyde (0.058 ml, 0.799 mmol) followed after 30 min by sodium triacetoxyborohydride (169 mg, 0.799 mmol) and AcOH (0.023 ml). The mixture was stirred at room temperature for 15 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 purified by chromatography eluting with 2% AcOEt in n-hexane to afford 57 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 purified by chromatography
  7. washeluting with 2% AcOEt in n-hexane

Sources & evidence

ORD record
ord-d4d6b3e406354c2985ab0c5b6bf67c0b
Source dataset
uspto-grants-2010_05
Patent number
US07714009B2

Reaction notes

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