3-Chloro-4-fluoroaniline → HCID 18916394, compound

HRID 1290638Notes

Reaction equation

HRID 1290638 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[F:9])[NH2:5].[CH3:10][O:11][C:12]([CH3:17])([CH3:16])[C:13](O)=[O:14].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:13](=[O:14])[C:12]([O:11][CH3:10])([CH3:17])[CH3:16])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

7

Reactant 4

HCID 97083-Chloro-4-fluoroanilineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 98554652-methoxy-2-methylpropanoic acid

Product 1

HCID 18916394HCID 18916394, compoundYield 48.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 6.1 grams (42 mmole) of 3-chloro-4-fluoroaniline, 5.0 grams (42 mmole) of 2-methoxy-2-methylpropanoic acid, and 10.5 grams (55 mmole) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 120 mL of methylene chloride was cooled to about 0° C., and 7.4 grams (55 mmole) of 1-hydroxybenzotriazole was added. Upon completion of the addition the reaction was slowly warmed to ambient temperature, where it stirred for about 18 hours. After this time the reaction mixture was poured into water, and the resulting mixture was filtered through diatomaceous earth to remove any salts that had precipitated. The organic layer was separated from the aqueous layer, washed with an aqueous saturated sodium chloride solution, dried with sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to a brown oil, which was passed through a silica gel scrub plug, yielding 5.0 grams of N-(3-chloro-4-fluorophenyl)-2-methoxy-2-methylpropionamide. The NMR spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of the addition the reaction
  2. filtrationthe resulting mixture was filtered through diatomaceous earth
  3. customto remove any salts that
  4. customhad precipitated
  5. customThe organic layer was separated from the aqueous layer
  6. washwashed with an aqueous saturated sodium chloride solution
  7. dry with materialdried with sodium sulfate
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated under reduced pressure to a brown oil, which

Sources & evidence

ORD record
ord-a31d757aef374130a719d8b0bb144aa3
Source dataset
uspto-grants-1998_05
Patent number
US05753595

Reaction notes

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