Chloroacetic Acid → HCID 18779028, compound

HRID 613745Notes

Reaction equation

HRID 613745 reaction equation
[H-].[Na+].[CH3:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][OH:11])=[CH:6][CH:5]=1.Cl[CH2:13][C:14]([OH:16])=[O:15]>CN(C)C=O>[CH3:3][C:4]1[S:8][C:7]([CH2:9][CH2:10][O:11][CH2:13][C:14]([OH:16])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 300Chloroacetic AcidHCID 24758Sodium hydrideHCID 1328928919498-70-5

Product 1

HCID 18779028HCID 18779028, compoundYield 107.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

Sodium hydride (0.622 g) was suspended in dry dimethylformamide (5 ml) and treated dropwise with a solution of 2-(5-methyl-2-thienyl)ethanol (1.0 g) in dry dimethylformamide (5 ml). The mixture was stirred at room temperature under nitrogen for 2 hours then a solution of chloroacetic acid (0.664 g) in dry dimethylformamide (5 ml) added. The mixture was stirred at room temperature overnight. The volatiles were removed in vacuo and the residue quenched with water and extracted with ethyl acetate. The aqueous layer was adjusted to pH 2 using dilute hydrochloric acid and then extracted with ethyl acetate. This extract was washed with water, brine then dried (MgSO4). The solvent was removed in vacuo to give a brown oil (1.51 g) which was used without further purification.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. customThe volatiles were removed in vacuo
  3. customthe residue quenched with water
  4. extractionextracted with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThis extract was washed with water, brine
  7. dry with materialthen dried (MgSO4)
  8. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-0acc2333a4114b17b227d3fd464cf235
Source dataset
uspto-grants-1999_12
Patent number
US06008365

Reaction notes

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