Hydrochloric Acid → HCID 68603120, compound

HRID 448873Notes

Reaction equation

HRID 448873 reaction equation
Br[CH2:2][CH2:3][CH2:4][OH:5].[Br:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:10]([N:12]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[OH:21])[CH3:13])=[O:11].C([O-])([O-])=O.[K+].[K+].Cl>CN(C=O)C>[Br:6][C:7]1[CH:8]=[C:9]([CH:22]=[CH:23][C:24]=1[Cl:25])[C:10]([N:12]([C:14]1[C:19]([CH3:20])=[CH:18][CH:17]=[CH:16][C:15]=1[O:21][CH2:2][CH2:3][CH2:4][OH:5])[CH3:13])=[O:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 123083-Bromo-1-propanolHCID 68602834HCID 68602834, compound

Product 1

HCID 68603120HCID 68603120, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Bromo-1-propanol (2.48 mL, 27.3 mmol) was added to a solution of 3-bromo-4-chloro-N-(2-hydroxy-6-methyl-phenyl)-N-methyl-benzamide (6.47 g, 18.3 mmol, Step 3B) in DMF (80 mL). To this was added K2CO3 (3.3 g, 24 mmol) and the mixture was stirred at room temperature for approximately 16 hrs. At this time the reaction was neutralized with 1N hydrochloric acid and the mixture was extracted with ethyl acetate. The organic layer was washed with first water and then brine solution. The organic filtrate was evaporated and the residue purified using column chromatography in a gradient of 50% ethyl acetate to 60% ethyl acetate in hexanes giving 3-bromo-4-chloro-N-[2-(3-hydroxy-propoxy)-6-methyl-phenyl]-N-methyl-benzamide (5.7 g, 76%). MS [M+H]+: 413.9; tR=2.29 min. (method 1)

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with first water
  3. customThe organic filtrate was evaporated
  4. customthe residue purified

Sources & evidence

ORD record
ord-2f4cf4e21eba4898b62608b27ee282c8
Source dataset
uspto-grants-2013_07
Patent number
US08481738B2

Reaction notes

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