Water → HCID 70289093, compound

HRID 1872077Notes

Reaction equation

HRID 1872077 reaction equation
[CH3:1][C:2]1[O:3][CH2:4][CH2:5][C:6]=1[C:7](Cl)=[O:8].[F:10][C:11]1[CH:17]=[CH:16][C:14](N)=[C:13](C2CCCCCCC2)[CH:12]=1.C([N:28]([CH2:31][CH3:32])[CH2:29][CH3:30])C.O>C1(C)C=CC=CC=1>[F:10][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:16][CH2:32][CH:31]([N:28]([C:7]([C:6]2[CH2:5][CH2:4][O:3][C:2]=2[CH3:1])=[O:8])[C:29]2[CH:30]=[CH:5][CH:6]=[CH:2][CH:1]=2)[CH2:17]1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 117447753-Furancarbonylchloride, 4,5-dihydro-2-methyl-HCID 15376472HCID 15376472, compound

Product 1

HCID 70289093HCID 70289093, compoundYield 132.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

At room temperature, a solution of 1.5 g (0.01 mol) of 2-methyl-4,5-dihydrofuran-3-carbonyl chloride in 10 ml of toluene is added dropwise with stirring to a mixture of 2.2 g (0.01 mol) of 4-fluoro-2-cyclooctylaniline, 1.0 g of triethylamine and 40 ml of toluene. After the addition has ended, the reaction mixture is stirred at room temperature for another 2 hours. The reaction mixture is subsequently admixed with water. The organic phase is separated off, dried over sodium sulphate and then concentrated under reduced pressure. The residue that remains is stirred with hexane. The resulting crystalline product is filtered off with suction and dried at 50° C. under reduced pressure. In this manner, 2.2 g (66.7% of theory) of N-(4-fluoro-2-cyclooctyl)-2-methyl-4,5-dihydrofuran-3-carboxanilide are obtained in the form of a solid substance of melting point 91° C.

Workup

  1. additionAfter the addition
  2. customThe organic phase is separated off
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. stirringThe residue that remains is stirred with hexane
  6. filtrationThe resulting crystalline product is filtered off with suction
  7. customdried at 50° C. under reduced pressure

Sources & evidence

ORD record
ord-be5437be0f9f4ff282a9bf959d856081
Source dataset
uspto-grants-2000_08
Patent number
US06107336

Reaction notes

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