Hydrochloric Acid → HCID 23369254, compound

HRID 1900540Notes

Reaction equation

HRID 1900540 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([OH:11])[CH:6]=[C:7]([CH3:10])[C:8]=1[NH2:9])[CH3:2].[OH-].[K+].Br[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20].Cl>CS(C)=O>[CH3:10][C:7]1[CH:6]=[C:5]([O:11][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:4]=[C:3]([CH2:1][CH3:2])[C:8]=1[NH2:9]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 84580Ethyl 5-bromovalerateHCID 233692554-Amino-3-ethyl-5-methylphenol

Product 1

HCID 23369254HCID 23369254, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
15 °C

Procedure

500 ml of dimethyl sulfoxide (DMSO) are introduced at room temperature and, while stirring vigorously, 52.1 g (338.6 mmol) of the 3-ethyl-4-amino-5-methylphenol prepared in stage 2 are added in small portions. The mixture is cooled to 15° C. Then 33.5 g (507.9 mmol) of aqueous 85% strength potassium hydroxide solution are added dropwise so that the reaction temperature does not exceed 20° C. Then 82.7 ml (507.9 mmol) of ethyl 5-bromovalerate are added dropwise over the course of 70 minutes, maintaining the reaction temperature at 25° C. After a homogeneous solution has formed it is added to a mixture of 130 ml of 4M hydrochloric acid and ice and stirred well. The aqueous mixture is washed with diethyl ether. The aqueous phase is then made alkaline with 2M NaOH and extracted with diethyl ether, and the ether phase is washed twice with water and then with saturated brine, dried over sodium sulfate and concentrated. 67.5 g of a viscous oil are obtained and purified by vacuum distillation. Yield 31.7 g (33.7% of theory), boiling point 151°-152° C./10-2Torr.

Workup

  1. customdoes not exceed 20° C
  2. temperaturemaintaining the reaction temperature at 25° C
  3. customAfter a homogeneous solution has formed it
  4. stirringstirred well
  5. washThe aqueous mixture is washed with diethyl ether
  6. extractionextracted with diethyl ether
  7. washthe ether phase is washed twice with water
  8. dry with materialwith saturated brine, dried over sodium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b3f4c251def548478b784b5ab2fa2c1f
Source dataset
uspto-grants-1996_11
Patent number
US05576188

Reaction notes

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