Mandelic Acid → HCID 18401127, compound

HRID 1019413Notes

Reaction equation

HRID 1019413 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH3:9])[CH:8]=1)[NH2:5].[C:10]([OH:20])(=O)[CH:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[OH:12].O.[OH:22]N1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[CH3:1][C:2]1[CH:3]=[C:4]([NH:5][C:10](=[O:20])[CH:11]([OH:12])[C:13]2[CH:18]=[CH:17][C:16]([OH:22])=[CH:15][CH:14]=2)[CH:6]=[C:7]([CH3:9])[CH:8]=1

Participants

7

Reactant 4

HCID 1292Mandelic AcidHCID 79493,5-DimethylanilineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 18401127HCID 18401127, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirring solution of 3,5-dimethylaniline (5.0 g, 41.3 mmol), mandelic acid (7.69 g, 41.3 mmol) and 1-hydroxybenzotriazole hydrate (6.14 g, 45.5 mmol) in dimethylformamide (100 mL) was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (8.73 g, 45.5 mmol) under nitrogen at room temperature. After stirring further for 16 hr, the reaction mixture was diluted with ethyl acetate (200 mL) and washed with 10% potassium hydrogen sulfate (2×50 mL), brine (50 mL), saturated sodium hydrogen carbonate (2×50 mL) and brine (50 mL). The organic phase was dried (MgSO4) and evaporated to give the product N-(3,5-Dimethyl-phenyl)-2-hydroxy-2-(4-hydroxy-phenyl) acetamide in 9.3 g yield.

Workup

  1. washwashed with 10% potassium hydrogen sulfate (2×50 mL), brine (50 mL), saturated sodium hydrogen carbonate (2×50 mL) and brine (50 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-dd30ba1b47b2483cb8eecf152472ad95
Source dataset
uspto-grants-2002_11
Patent number
US06486342B1

Reaction notes

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