Hydrochloric Acid → HCID 20800561, compound

HRID 1296735Notes

Reaction equation

HRID 1296735 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.O[NH:9][C:10](=[NH:21])[C:11]1[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=1.N1C=CC=CC=1.Cl>C1(C)C=CC=CC=1.O>[CH3:6][C:5]1[O:7][N:21]=[C:10]([C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[C:13]([N+:18]([O-:20])=[O:19])[CH:12]=2)[N:9]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 178425644HCID 178425644, compound

Product 1

HCID 20800561HCID 20800561, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

Acetic anhydride (25 mL, 260 mmol) was added to a solution of compound 1a (11.5 g, 58.8 mmol) in a mixture of pyridine (50 mL, 620 mmol) and toluene (200 mL). The reaction mixture was refluxed for 22 h. After cooling to rt, a solution of concentrated HCl (75 mL) in water (200 mL) was added, and the aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated in vacuo. The residue was recrystallized from absolute ethanol to afford compound 1b as tan needles (9.8 g, 76%). ESI-MS m/e 220.2 (M+1).

Workup

  1. temperatureThe reaction mixture was refluxed for 22 h
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layers were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from absolute ethanol

Sources & evidence

ORD record
ord-767d6cd9a6fb43f3b2cc298eaa26d9da
Source dataset
uspto-grants-2007_07
Patent number
US07247654B2

Reaction notes

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