Diethylamine → HCID 19594847, compound

HRID 612600Notes

Reaction equation

HRID 612600 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][CH:14]=[CH:15][C:16]=1[O:17][CH3:18])([CH3:3])[CH3:2].S(Cl)(Cl)=O.[CH2:26]([NH:28][CH2:29][CH3:30])[CH3:27]>C(Cl)Cl>[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])=[C:16]([O:17][CH3:18])[CH:15]=[CH:14][CH:13]=1)=[O:21])[CH3:27]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 24386Thionyl ChlorideHCID 19594924HCID 19594924, compound

Product 1

HCID 19594847HCID 19594847, compoundYield 111.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Prepare a stirred solution of 2'-isopropoxy-6-methoxy-biphenyl-2-carboxylic acid (1.432 g, 0.0050 mole) in methylene chloride (50 mL) at -50° C. and under argon. Warm to ambient temperature then add thionyl chloride (0.8415 g, 0.516 mL). Continue stirring for about 45 minutes, observing the color change to light brown. Cool to 0° C. and dropwise add diethylamine (6.00 mL, 4.242 g, 0.058) mole, keeping the temperature of the reaction below 26° C. Continue stirring for about 30 minutes once the addition is complete. Dilute to 150 mL with additional methylene chloride. Wash the methylene chloride layer with water, separate, and extract twice with 100 mL 5% sodium bicarbonate. Separate, wash again with brine , separate and dry over MgSO4. Filter through celite and condense on a rotary evaporator to a light brown, viscous liquid. Elute via chromatography with 30% ethyl acetate/70% hexane to give a clear viscous liquid (1.90 g). Concentrate under high vacuum to give a waxy solid of the title compound. (1.40 g, 82%).

Workup

  1. temperatureCool to 0° C.
  2. customthe temperature of the reaction below 26° C
  3. stirringContinue stirring for about 30 minutes once the addition
  4. washWash the methylene chloride layer with water
  5. customseparate
  6. extractionextract twice with 100 mL 5% sodium bicarbonate
  7. customSeparate
  8. washwash again with brine
  9. customseparate
  10. dry with materialdry over MgSO4
  11. filtrationFilter through celite and condense on a rotary evaporator to a light brown, viscous liquid
  12. washElute via chromatography with 30% ethyl acetate/70% hexane

Sources & evidence

ORD record
ord-f6e0fd76b82941bf8499bcc726afdbc6
Source dataset
uspto-grants-1999_12
Patent number
US06004959

Reaction notes

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