Hydrochloric Acid → HCID 58188286, compound

HRID 1845243Notes

Reaction equation

HRID 1845243 reaction equation
[H-].[Na+].[CH:3]1([SH:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17](Br)[CH:18]=1)[C:13]([OH:15])=[O:14].Cl>CS(C)=O.O>[Br:9][C:10]1[CH:11]=[C:12]([CH:16]=[C:17]([S:8][CH:3]2[CH2:7][CH2:6][CH2:5][CH2:4]2)[CH:18]=1)[C:13]([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 12063Benzoic acid, 3,5-dibromo-HCID 15510CyclopentanethiolHCID 24758Sodium hydride

Product 1

HCID 58188286HCID 58188286, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 962WaterSolvent

Procedure

To a stirred mixture of sodium hydride (60% in mineral oil, 0.82 g, 20.5 mmol) and DMSO (15 mL) in a sealable flask at 0° C. was slowly added cyclopentanethiol (1.23 mL, 11.9 mmol). The mixture was stirred at room temperature for 30 min and then a solution of 3,5-dibromobenzoic acid (2.5 g, 8.9 mmol) in DMSO (10 mL) was added. The reaction was sealed and stirred at 80° C. overnight. After cooling, the reaction mixture was poured into water and adjusted to pH 5-6 with 15% HCl (aq.) and extracted with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated to afford the crude product which was used for the next step reaction without further purification.

Workup

  1. customThe reaction was sealed
  2. stirringstirred at 80° C. overnight
  3. temperatureAfter cooling
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-65fb1a74e9c84de3ba166b329308a2c2
Source dataset
uspto-grants-2015_02
Patent number
US08946439B2

Reaction notes

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