Thioglycolic Acid → HCID 11459551, compound

HRID 456583Notes

Reaction equation

HRID 456583 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][OH:10])=[CH:4][C:3]=1[N+:11]([O-:13])=[O:12].[SH:14][CH2:15][C:16]([OH:18])=[O:17].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[OH:10][CH2:9][CH2:8][C:5]1[CH:6]=[CH:7][C:2]([S:14][CH2:15][C:16]([OH:18])=[O:17])=[C:3]([N+:11]([O-:13])=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 1133Thioglycolic AcidHCID 11430Potassium CarbonateHCID 11252405HCID 11252405, compound

Product 1

HCID 11459551HCID 11459551, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 2-(4-fluoro-3-nitro-phenyl)ethanol [RN20274-69-5](1.1 g, 6 mmol), mercaptoacetic acid (0.61 g, 6.6 mmol), potassium carbonate (2.8 g, 20 mmol) and N,N-dimethylformamide (12 ml) was heated at 70° C. for 4 hours. The mixture was poured onto water (200 ml) and the aqueous phase was washed with ethyl acetate. The aqueous phase was then acidified with 1M aqueous hydrochloric acid and extracted three times with dichloromethane. The extracts were dried and evaporated to give an oil (0.92 g, 60%).

Workup

  1. additionThe mixture was poured onto water (200 ml)
  2. washthe aqueous phase was washed with ethyl acetate
  3. extractionextracted three times with dichloromethane
  4. customThe extracts were dried
  5. customevaporated

Sources & evidence

ORD record
ord-dc6e5b3f5b874c3da4eea6db501b57a3
Source dataset
uspto-grants-2007_03
Patent number
US07186730B2

Reaction notes

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