Hydrochloric Acid → HCID 86600354, compound

HRID 29716Notes

Reaction equation

HRID 29716 reaction equation
[OH:1][NH:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]=2[N:21]([CH3:23])[CH3:22])=[O:15])=[CH:6][CH:5]=1.[ClH:29].O>CC(O)C>[ClH:29].[OH:1][NH:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH2:12][NH:13][C:14]([C:16]2[O:17][C:18]3[CH:27]=[CH:26][CH:25]=[CH:24][C:19]=3[C:20]=2[N:21]([CH3:23])[CH3:22])=[O:15])=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 86600351HCID 86600351, compound

Product 1

HCID 86600354HCID 86600354, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

N-hydroxy-4-[2-(3-dimethylaminobenzofuran-2-ylcarbonylamino)ethoxy]-benzamide (22.7 g, 0.057 mol) was suspended in 2-propanol (220 ml). 12 M HCl (5.2 ml, 0.063 mol) was added in one portion and the resulting mixture was heated to reflux. Water (44 ml) was added dropwise until a homogenous solution was obtained. The reaction mixture was allowed to cool and crystallize overnight. After cooling below 5° C. for one h, the crystals were filtered and washed with 2-propanol before being dried in vacuo to give the title compound (22.0 g) as a white solid.

Workup

  1. temperaturethe resulting mixture was heated to reflux
  2. customwas obtained
  3. temperatureto cool
  4. customcrystallize overnight
  5. temperatureAfter cooling below 5° C. for one h
  6. filtrationthe crystals were filtered
  7. washwashed with 2-propanol
  8. custombefore being dried in vacuo

Sources & evidence

ORD record
ord-b907513d7a934faaa145487b1e24a4e0
Source dataset
uspto-grants-2008_09
Patent number
US07420089B2

Reaction notes

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