Diethylamine → HCID 19594892, compound

HRID 612594Notes

Reaction equation

HRID 612594 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[C:11]1[C:12]([C:19]([OH:21])=O)=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27].C(OCC)(=O)C>C(Cl)Cl.CCCCCC>[CH2:26]([N:28]([CH2:29][CH3:30])[C:19]([C:12]1[C:11]([C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[O:4][CH:1]([CH3:2])[CH3:3])=[CH:16][CH:15]=[C:14]([O:17][CH3:18])[CH:13]=1)=[O:21])[CH3:27]

Participants

7

Reactant 4

HCID 8021DiethylamineHCID 8857Ethyl AcetateHCID 24386Thionyl ChlorideHCID 19594850HCID 19594850, compound

Product 1

HCID 19594892HCID 19594892, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

Prepare a solution of 2'-isopropoxy-4-methoxy-biphenyl-2-carboxylic acid (4.80 g, 0.0168 mole) in 125 mL methylene chloride (dichloromethane). Under an argon atmosphere, at ambient conditions, add thionyl chloride (2.99 g, 0.0356 mole, 1.835 mL). Continue stirring for about 45 minutes, observing the color change to light brown. Cool the reaction mixture to 0° C. and dropwise add diethylamine (22.00 mL, 15.627 g, 0.21 mole), ensuring the temperature does not exceed 25° C. Continue stirring for 30 minutes after addition of the amine is complete. Dilute the reaction to 150 mL of methylene chloride and wash the organic phase with water, separate and wash twice with 100 mL 5% sodium bicarbonate. Separate and wash with brine (sat'd NaCl) and dry over magnesium sulfate. Filter through celite and evaporate on a rotary evaporator to give a viscous light brown liquid. Chromatography (30% ethyl acetate: 70% hexane) gives a pale yellow liquid. Place under near vacuum to give a waxy solid of the title compound (3.80 g, 66%).

Workup

  1. customdoes not exceed 25° C
  2. stirringContinue stirring for 30 minutes
  3. additionDilute
  4. washwash the organic phase with water
  5. customseparate
  6. washwash twice with 100 mL 5% sodium bicarbonate
  7. customSeparate
  8. washwash with brine (sat'd NaCl)
  9. dry with materialdry over magnesium sulfate
  10. filtrationFilter through celite
  11. customevaporate on a rotary evaporator
  12. customto give a viscous light brown liquid

Sources & evidence

ORD record
ord-a5d278a88a314f8fb6557acacff1342e
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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