Dimethylamine → HCID 17842470, compound

HRID 2096217Notes

Reaction equation

HRID 2096217 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]=O.[CH3:8][NH:9][CH3:10].[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl>[CH3:8][N:9]([CH3:10])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 27349031,3-Thiazole-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 17842470HCID 17842470, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of thiazole-2-carbaldehyde (Aldrich, 2.0 g, 17.7 mmol) in DCM (20 mL) was treated with dimethylamine (Aldrich, 40% in water, 3 mL) and molecular sieves (˜1.0 g) followed by NaBH(OAc)3 (4.2 g, 20 mmol). The reaction was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give yellow solid, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as yellow solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was partitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give yellow solid, which
  8. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-833de142593c4d80a02c8876000cd9f0
Source dataset
uspto-grants-2013_05
Patent number
US08450304B2

Reaction notes

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