Hydrochloric Acid → HCID 86650090, compound

HRID 1639881Notes

Reaction equation

HRID 1639881 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:18]([O-:20])=[O:19])[C:13]([O:15]CC)=[O:14].NC(N)=[S:23].[OH-].[Na+].Cl>C(O)C>[SH:23][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH:12]([C:18]([OH:20])=[O:19])[C:13]([OH:15])=[O:14]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 2723790ThioureaHCID 86650091HCID 86650091, compound

Product 1

HCID 86650090HCID 86650090, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Reflux a solution of ethyl 2-(10-bromo-decyl)malonate (5.5 mmole) and thiourea (6.6 mmole) in 95% ethanol (25 mL) for 5 hours and then add an aqueous NaOH (2.0 M, 25 mL) and reflux for another 15 hours. Then, add an aqueous HCl (2.0 M) until the solution becomes acidic (approximately pH ˜2). Extract the reaction mixture with ether three times and wash and dry the combined organic layers with saturated NaCl solution with MgSO4. The product, 2-(10-mercaptodecyl)-propanedioic acid, can then be obtained by removal of solvent under reduced pressure.

Workup

  1. temperaturereflux for another 15 hours
  2. extractionExtract the reaction mixture with ether three times
  3. washwash
  4. dry with materialdry the combined organic layers with saturated NaCl solution with MgSO4

Sources & evidence

ORD record
ord-8cd24c3b8da046948caccd85e4c33904
Source dataset
uspto-grants-2012_02
Patent number
US08110605B2

Reaction notes

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