2-Chloroethanol → HCID 53258885, compound

HRID 2206997Notes

Reaction equation

HRID 2206997 reaction equation
[CH:1]([O:4][C:5](=[O:20])[CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([NH2:19])=[CH:18][C:11]=2[N:10]=1)([CH3:3])[CH3:2].[OH2:21].Cl[CH2:23][CH2:24][OH:25].C(N([CH2:31][CH3:32])CC)C>C(OCC)(=O)C.CCCCCC>[CH:1]([O:4][C:5](=[O:20])[CH2:6][CH2:7][CH2:8][C:9]1[N:13]([CH3:14])[C:12]2[CH:15]=[CH:16][C:17]([N:19]([CH2:32][CH2:31][OH:21])[CH2:23][CH2:24][OH:25])=[CH:18][C:11]=2[N:10]=1)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 342-Chloroethanol4×HCID 962Water2×HCID 8471Triethylamine4×HCID 53258887HCID 53258887, compound

Product 1

HCID 53258885HCID 53258885, compound

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
72.5 °C

Procedure

4-(5-Amino-1-methyl-1H-benzoimidazol-2-yl)-butyric acid isopropyl ester (15.0 g), water (30 mL), 2-chloroethanol (15.6 mL, 4.0 M) and triethyl amine (22.7 mL 3.0 M), are charged into a round bottom flask and stirred. The reaction mixture is heated to about 70-75° C. and maintained for about 2 hours. 2-Chloroethanol (7.8 mL, 2.0 M) and triethylamine (22.7 mL, 3.0 M) are added to the reaction mixture and stirred at the same temperature for about 90 minutes. 2-Chloroethanol (7.8 mL, 2.0 M) and triethylamine (22.7 mL, 3.0 M) are added to the reaction mixture and stirred at the same temperature for about 2 hours. 2-Chloroethanol (7.8 mL, 2.0 M) is added to the reaction mixture and stirred at the same temperature for about 4 hours. Triethylamine (11.3 mL, 1.5 M) is added to the reaction mixture and maintained at the same temperature for about 4 hours. The reaction mixture is cooled to 25-30° C., then dematerialized water (300 mL) is added and stirred. The reaction mass is extracted with dichloromethane (3×150 mL). The obtained dichloromethane extract is washed with saturated sodium bicarbonate solution (150 mL), followed by saturated sodium chloride (150 mL), and dried over sodium sulfate. The dichloromethane layer is concentrated under vacuum at about 40-45° C. to give a residue, which is dissolved in ethyl acetate (75 mL) and concentrated at 40-45° C. under vacuum to give a viscous mass. The obtained mass is dissolved in ethyl acetate (45 mL), then n-hexane (225 mL) is added slowly at 27° C. and stirred for 1 hour. The obtained solid is collected by filtration, washed, and dried in a vacuum oven at 45-50° C. for about 4-5 hours, to give the title compound. Yield: 13.0 g (68%).

Workup

  1. temperaturemaintained for about 2 hours
  2. stirringstirred at the same temperature for about 90 minutes
  3. stirringstirred at the same temperature for about 2 hours
  4. stirringstirred at the same temperature for about 4 hours
  5. temperaturemaintained at the same temperature for about 4 hours
  6. temperatureThe reaction mixture is cooled to 25-30° C.
  7. additionis added
  8. stirringstirred
  9. extractionThe reaction mass is extracted with dichloromethane (3×150 mL)
  10. extractionThe obtained dichloromethane extract
  11. washis washed with saturated sodium bicarbonate solution (150 mL)
  12. dry with materialdried over sodium sulfate
  13. concentrationThe dichloromethane layer is concentrated under vacuum at about 40-45° C.
  14. customto give a residue, which
  15. concentrationconcentrated at 40-45° C. under vacuum
  16. customto give a viscous mass
  17. stirringstirred for 1 hour
  18. filtrationThe obtained solid is collected by filtration
  19. washwashed
  20. customdried in a vacuum oven at 45-50° C. for about 4-5 hours

Sources & evidence

ORD record
ord-492c1919fde9457fa5f57b559db630ec
Source dataset
uspto-grants-2016_06
Patent number
US09376394B2

Reaction notes

Loading…