Benzoic Acid → HCID 178507854, compound

HRID 2271425Notes

Reaction equation

HRID 2271425 reaction equation
[CH:1]1[C:2]([NH2:15])=[N+:3]([O-:14])[C:4]([NH2:13])=[N:5][C:6]=1[N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.C(O)(C)C.[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O>[CH:1]1[C:2]([NH2:15])=[N+:3]([O-:14])[C:4]([NH2:13])=[N:5][C:6]=1[N:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1.[C:20]([OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 243Benzoic Acid2×HCID 3776Isopropanol2×HCID 178507853HCID 178507853, compound2×

Product 1

HCID 178507854HCID 178507854, compoundYield 94.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
69 °C

Procedure

A 250 mL round bottom flask was charged with solid minoxidil (21.209 g), 85 mL isopropanol, and 85 mL water. The system was heated from room temperature to approximately 75° C. with stirring, until the solids dissolved. A 50 mL round bottom flask was charged with benzoic acid (12.421 g), 21 mL of isopropanol, and 21 mL of water. The system was heated from room temperature to approximately 75° C. with stirring, until the solids dissolved. The benzoic acid solution was added to the minoxidil solution and the resulting system was cooled to approximately 69° C. and held at this temperature for one hour. Precipitation of white solids was observed. The system was slowly cooled to room temperature before being placed in a refrigerator with stirring for about one day. Solids were collected by vacuum filtration and dried under vacuum at room temperature, yielding 31.8 g of minoxidil:benzoic acid 1:1 monohydrate cocrystal (90% yield).

Workup

  1. temperatureThe system was heated from room temperature to approximately 75° C.
  2. dissolutiondissolved
  3. temperatureThe system was heated from room temperature to approximately 75° C.
  4. stirringwith stirring, until the solids
  5. dissolutiondissolved
  6. customPrecipitation of white solids
  7. temperatureThe system was slowly cooled to room temperature
  8. stirringwith stirring for about one day
  9. filtrationSolids were collected by vacuum filtration
  10. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-64a1d05d263f4a53800dfe667b743932
Source dataset
uspto-grants-2015_09
Patent number
US09120766B2

Reaction notes

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