3-Mercaptopropionic Acid → HCID 54037362, compound

HRID 1462455Notes

Reaction equation

HRID 1462455 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[OH-].[Na+].[C:9]1([C:14](Cl)=[O:15])[S:13][CH:12]=[CH:11][CH:10]=1.C([O-])(O)=O.[Na+]>C(OCC)C.O>[C:9]1([C:14]([S:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:15])[S:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 4

HCID 65143-Mercaptopropionic AcidHCID 14798Sodium HydroxideHCID 789282-Thiophenecarbonyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 54037362HCID 54037362, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A mixture of 26.5 g (0.25 mol) of 3-mercaptopropionic acid, 150 mls of ethyl ether and 250 mls of 1-normal NaOH has been treated dropwise, the temperature being maintained between 0° C. and 5° C., with vigorous stirring, with 40.3 g of 2-thenoyl chloride (0.275 mol) in 80 mls of ethyl ether, while concurrently adding, so as to keep the pH of the reaction environment constantly alkaline, 31.5 g (0.36 mol) of NaHCO3 in 800 mls of water. On completion of dripping, stirring has been continued for 16 additional hours at room temperature. Upon separation of the organic phase, the waters have been extracted with ethyl ether again, and then made acidic with 4-normal hydrochloric acid. The as-formed precipitate has been recrystallized from 70% ethanol.

Workup

  1. additionhas been treated dropwise
  2. additionwhile concurrently adding
  3. customhas been continued for 16 additional hours at room temperature
  4. customUpon separation of the organic phase
  5. extractionthe waters have been extracted with ethyl ether again
  6. customThe as-formed precipitate has been recrystallized from 70% ethanol

Sources & evidence

ORD record
ord-4cec23bec0fe40d5a21dce19a3af780f
Source dataset
uspto-grants-1984_07
Patent number
US04460601

Reaction notes

Loading…