3-(Dimethylamino)phenol → HCID 58006189, compound

HRID 215913

Reaction equation

HRID 215913 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([OH:10])[CH:5]=1)[CH3:3].Cl[CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14].C([O-])([O-])=O.[K+].[K+]>CS(C)=O.ClCCl>[CH3:1][N:2]([CH3:3])[C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[O:10][CH2:12][C:13]([N:15]([CH3:17])[CH3:16])=[O:14]

Participants

6

Reactant 3

HCID 74213-(Dimethylamino)phenolHCID 11430Potassium CarbonateHCID 758862-chloro-N,N-dimethylacetamide

Product 1

HCID 58006189HCID 58006189, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 3-N,N-dimethylamino phenol (69) (3.43 g, 25 mmol) and 2-chloro N,N-dimethylacetamide (3.66 g, 30 mmol) in DMSO (30 mL) was added K2CO3 (6.7 g, 50 mmol) and the resulting suspension was stirred at room temperature for 16 h. The reaction was then diluted with dichloromethane (125 mL), and washed with water (2×100 mL), and brine (100 mL), and dried, and filtered, and the solvent was removed under vacuum. The crude product, Compound 70, was obtained as purple, thick oil that was used in the next step without additional purification.

Workup

  1. washwashed with water (2×100 mL), and brine (100 mL)
  2. customdried
  3. filtrationfiltered
  4. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-8c0bde69592943d7a6750f0b57894054
Source dataset
uspto-grants-2012_06
Patent number
US08193203B2

Linked notes

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