Dicyclohexylcarbodiimide → HCID 18183268, compound

HRID 1359512Notes

Reaction equation

HRID 1359512 reaction equation
[Br:1][CH:2]([CH3:6])[C:3](O)=[O:4].[CH3:7][NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[F:15].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl>[F:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]([CH3:7])[C:3](=[O:4])[CH:2]([Br:1])[CH3:6]

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 117292-Bromopropionic acidHCID 27590102-Fluoro-N-methylaniline

Product 1

HCID 18183268HCID 18183268, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Bromopropionic acid (3.4 g, 0.022 mol) and N-methyl-2-fluoroaniline(3 g. 0.024 mol) were dissolved in 50 ml of chloroform and cooled to 0° C. A solution of dicyclohexylcarbodiimide(5 g, 0.024 mol) in 10 ml of chloroform was slowly injected through a syringe. A temperature of the reaction mixture was raised to room temperature and it was stirred for 1 hour. Solid remained during the reaction was filtered out and washed twice with 20 ml of chloroform. The filtrate was concentrated under reduced pressure and the crude product was purified by column chromatography (eluent; ethyl acetate/n-hexane=⅓) to afford 5 g of the target product.

Workup

  1. temperatureA temperature of the reaction mixture was raised to room temperature
  2. filtrationwas filtered out
  3. washwashed twice with 20 ml of chloroform
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe crude product was purified by column chromatography (eluent; ethyl acetate/n-hexane=⅓)

Sources & evidence

ORD record
ord-b314bd09a9f24468856754cbfdf52ad4
Source dataset
uspto-grants-2003_07
Patent number
US06600048B2

Reaction notes

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