Methanol → HCID 178497550, compound

HRID 404259Notes

Reaction equation

HRID 404259 reaction equation
Cl.[NH:2]1[CH:6]=[C:5]([C:7]2[CH:15]=[CH:14][C:10]([C:11]([OH:13])=[O:12])=[CH:9][CH:8]=2)[N:4]=[CH:3]1.S(Cl)(Cl)=O.[CH3:20]O>>[NH:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:11]([O:13][CH3:20])=[O:12])=[CH:14][CH:15]=2)[N:4]=[CH:3]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 178479743HCID 178479743, compound

Product 1

HCID 178497550HCID 178497550, compoundYield 86%

Procedure

To a stirred solution of 4-(1H-imidazol-4-yl)benzoic acid hydrochloride (20 mg, 0.089 mmol) at 0° C. in MeOH (5 mL) was added thionyl chloride (11.6 mg, 0.097 mmol) and the solution was allowed to warm to rt. After stirring overnight the solution was concentrated under reduced pressure to dryness and the crude residue was partitioned between EtOAc (25 mL) and sat'd NaHCO3 (5 mL). The organic layer was collected, dried (Na2SO4) and concentrated under reduced pressure to afford the desired product as a pale yellow solid (15 mg, 86% yield). 1H NMR: 3.92 (s, 3H), 7.41 (s, 1H), 7.67-7.77 (m, 3H), 8.03 (s, 2H).

Workup

  1. concentrationwas concentrated under reduced pressure to dryness
  2. customthe crude residue was partitioned between EtOAc (25 mL) and sat'd NaHCO3 (5 mL)
  3. customThe organic layer was collected
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-61776d565bb947ee94c8aea57ae5f07d
Source dataset
uspto-grants-2014_06
Patent number
US08748469B2

Reaction notes

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