Dimethylamine → Ethyl 4-((dimethylamino)methyl)-2-phenylthiazole-5-carboxylate

HRID 2407710Notes

Reaction equation

HRID 2407710 reaction equation
Br[CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9].[CH3:19][NH:20][CH3:21]>O1CCCC1>[CH3:19][N:20]([CH2:2][C:3]1[N:4]=[C:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[S:6][C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH3:21]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 12736369Ethyl 4-(bromomethyl)-2-phenyl-1,3-thiazole-5-carboxylate

Product 1

HCID 58504082Ethyl 4-((dimethylamino)methyl)-2-phenylthiazole-5-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound prepared in Example 126 (1.00 g) was suspended in tetrahydrofuran (20 mL) and dimethylamine (2 M) (7.66 mL) added and the reaction mixture stirred at room temperature for 3 hours. The reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organics were washed with brine, dried, magnesium sulfate and concentrated under reduced pressure to afford the crude material, which was purified by flash column chromatography to afford the title compound (0.65 g) having the following physical data.

Workup

  1. customThe reaction mixture was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  2. washThe organics were washed with brine
  3. customdried
  4. concentrationmagnesium sulfate and concentrated under reduced pressure
  5. customto afford the crude material, which
  6. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-42a633a0fbe84b0dabfd42ed91215914
Source dataset
uspto-grants-2014_08
Patent number
US08809538B2

Reaction notes

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