Methanol → HCID 178497550, compound

HRID 705429Notes

Reaction equation

HRID 705429 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-5d848978cf344404a33cd4f1e1c6e6e0
Source dataset
uspto-grants-2015_11
Patent number
US09174942B2

Reaction notes

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