Dimethylamine → HCID 178484513, compound

HRID 1858504Notes

Reaction equation

HRID 1858504 reaction equation
[H-].[Na+].[CH3:3][N:4]([CH3:7])[CH:5]=[O:6].CNC.[SH:11][C:12]1[S:13][CH:14]=[C:15]([CH2:17]C(OCC)=O)[N:16]=1>O1CCCC1.C(OCC)(=O)C.O>[CH3:3][N:4]([CH3:7])[C:5](=[O:6])[CH2:17][C:15]1[N:16]=[C:12]([SH:11])[S:13][CH:14]=1

Participants

8

Reactant 4

HCID 674DimethylamineHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 178470768HCID 178470768, compound

Product 1

HCID 178484513HCID 178484513, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of sodium hydride (24 mg) and N,N-dimethylformamide (4.0 ml) was added a solution of dimethylamine (54 mg) in tetrahydrofuran (320 μl) at -10° C. After stirring at room temperature for 1 hour, ethyl 2-mercapto-4-thiazole acetate (203 mg) was added to the mixture at room temperature. After stirring at room temperature for 3 hours, the mixture was poured into a mixture of water and ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over magnesium sulfate and evaporated under reduced pressure. The residue was subjected to column chromatography on silica gel (eluent: ethyl acetate) to give N,N-dimethyl-2-mercapto-4-thiazole acetamide (72 mg).

Workup

  1. stirringAfter stirring at room temperature for 3 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ef72d88c3d5c481b9e7aef0d8cf6f116
Source dataset
uspto-grants-2000_11
Patent number
US06150351

Reaction notes

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