Hydrochloric Acid → HCID 57446112, compound

HRID 1803810Notes

Reaction equation

HRID 1803810 reaction equation
[OH-].[Na+].[OH:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1.[CH2:17](Br)[C:18]#[CH:19].Cl>CO.CN(C=O)C.O>[CH2:19]([O:3][C:4]1[CH:16]=[CH:15][C:7]2[N:8]=[C:9]([S:11]([NH2:14])(=[O:13])=[O:12])[S:10][C:6]=2[CH:5]=1)[C:18]#[CH:17]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 7842Propargyl bromideHCID 14798Sodium HydroxideHCID 68521296-Hydroxy-1,3-benzothiazole-2-sulfonamide

Product 1

HCID 57446112HCID 57446112, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of NaOH in MeOH (2.5 M, 18.8 mL) and DMF (60 mL) was added 1 (4.33 g, 18.8 mmol). The mixture was allowed to stir for 45 min at 23° C. before propargyl bromide (80% in PhMe, 3.36 mL, 22.56 mmol) was added slowly over 10 min. After 2.5 h, an aqueous solution of 1 M HCl was added to achieve pH=6, where upon a white precipitate forms. Water was then added and the organic layer was extracted 3×EtOAc and the combined organic extracts washed 1×H2O, 1×brine, and then dried over MgSO4. The solvents were removed in vacuo and the crude residue purified by flash chromatography using Hexanes:EtOAc on a Biotage purification system to yield 3 as a pale yellow solid (1.43 g, 29%).

Workup

  1. additionwas added slowly over 10 min
  2. extractionthe organic layer was extracted 3×EtOAc
  3. washthe combined organic extracts washed 1×H2O, 1×brine
  4. dry with materialdried over MgSO4
  5. customThe solvents were removed in vacuo
  6. customthe crude residue purified by flash chromatography
  7. customEtOAc on a Biotage purification system

Sources & evidence

ORD record
ord-0f6f329aa38b4379b4aa11e4c0d60001
Source dataset
uspto-grants-2013_01
Patent number
US08354092B2

Reaction notes

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