Bromoacetic Acid → HCID 19851324, compound

HRID 1606888Notes

Reaction equation

HRID 1606888 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH3:10])=[O:8].S.[Na].BrC[C:20]([OH:22])=[O:21]>CO>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)[C:7]([O:9][CH2:10][C:20]([OH:22])=[O:21])=[O:8]

Participants

5

Reactant 3

HCID 6227Bromoacetic AcidHCID 15665029HCID 15665029, compoundHCID 86586439Sodium hydrogen sulphide

Product 1

HCID 19851324HCID 19851324, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a well stirred solution of methyl dithiophenylacetate (16.2 grams, 0.089 mole) in methanol (50 mL) was added anhydrous sodium hydrogen sulfide (5.6 grams, 0.10 mole). The mixture was stirred overnight at room temperature, and the solvent removed in vacuo. The solid salt thus obained was taken up in tetrahydrofuran (125 mL). To the solution was added bromoacetic acid (12.4 grams, 0.089 mole). The resulting mixture was stirred for 2 hours at room temperature, and the solvent removed in vacuo. The resulting solid was taken up in 5% (w/v) aqueous sodium bicarbonate, then washed twice with chloroform. The aqueous layer was acidified by the addition of concentration HCl and then extracted three times into diethyl ether. The combined ethereal extracts were dried over anhydrous Na2SO4. The solvent was then finally removed in vacuo to afford carboxymethyl dithiophenylacetate, an orange solid, in 94.5% yield.

Workup

  1. customthe solvent removed in vacuo
  2. stirringThe resulting mixture was stirred for 2 hours at room temperature
  3. customthe solvent removed in vacuo
  4. washwashed twice with chloroform
  5. additionThe aqueous layer was acidified by the addition of concentration HCl
  6. extractionextracted three times into diethyl ether
  7. dry with materialThe combined ethereal extracts were dried over anhydrous Na2SO4
  8. customThe solvent was then finally removed in vacuo

Sources & evidence

ORD record
ord-b5b7ffd6de754240b19ce46298eee2b5
Source dataset
uspto-grants-1989_09
Patent number
US04863870

Reaction notes

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