Hydrochloric Acid → HCID 178478856, compound

HRID 705423Notes

Reaction equation

HRID 705423 reaction equation
[NH:1]1[C:5]([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:12]C(=O)OC(C)(C)C)=[CH:4][N:3]=[CH:2]1.[ClH:20]>O1CCOCC1>[Cl-:20].[NH3+:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[C:5]1[N:1]=[CH:2][NH2+:3][CH:4]=1.[Cl-:20]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 58294196HCID 58294196, compound

Product 1

HCID 178478856HCID 178478856, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of tert-butyl 2-(1H-imidazol-5-yl)phenylcarbamate (64.7 mg, 0.25 mmol) in 1,4-dioxane (2 mL) was added HCl (2 mL, 2.0 M in 1,4-dioxane). The mixture was allowed to stir at room temperature for 12 h and concentrated under reduced pressure. The residue was diluted with ethyl ether and the desired hydrochloride salt was precipitated. The colorless solid was collected by filtration, which afforded the desired product in 46% yield. 1H NMR: 6.66-6.82 (m, 2H), 7.11-7.20 (m, 2H), 7.21-7.38 (m, 4H), 7.40-7.68 (m, 3H).

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with ethyl ether
  3. customthe desired hydrochloride salt was precipitated
  4. filtrationThe colorless solid was collected by filtration, which

Sources & evidence

ORD record
ord-685af054600145d3b4863770d563c696
Source dataset
uspto-grants-2015_11
Patent number
US09174942B2

Reaction notes

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