Benzaldehyde → HCID 67773638, compound

HRID 1963076Notes

Reaction equation

HRID 1963076 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][CH2:9][N+:10]([O-:12])=[O:11])[C:3]=1[CH3:13].[CH:14](=O)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1(C)C=CC=CC=1.C(N)CCC.C(O)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH2:8][C:9]([N+:10]([O-:12])=[O:11])=[CH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:3]=1[CH3:13]

Participants

6

Reactant 2

HCID 240Benzaldehyde2×HCID 677734531-Fluoro-2-methyl-3-(2-nitroethyl)benzene

Product 1

HCID 67773638HCID 67773638, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalyst2×HCID 8007ButylamineCatalyst2×HCID 1140TolueneSolvent

Procedure

The compound of step 2 (17.951 g, 98 mmol), benzaldehyde (10.43 ml, 102.90 mmol), n-butylamine (0.49 ml, 4.90 mmol) and acetic acid (0.28 ml, 4.90 mmol) in 49 ml of toluene were heated at 180° C. in a Dean-Stark apparatus for 6 h. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The residue was taken up in 49 ml of toluene, benzaldehyde (10.43 ml, 102.90 mmol), n-butylamine (0.49 ml, 4.90 mmol) and acetic acid (0.28 ml, 4.90 mmol) were added, and the mixture was heated at 180° C. in a Dean-Stark apparatus for 3 h. After cooling to room temperature, the mixture was evaporated to dryness under reduced pressure. The residue was triturated with 25 ml of diethyl ether/pentane (1:1). The solid was filtered off, rinsed with cyclohexane, and dissolved in 75 ml of DCM. The solution was dried with magnesium sulfate and evaporated to dryness to give 21.57 g of the title compound as a yellow solid melting at 111-112° C.

Workup

  1. customthe mixture was evaporated to dryness under reduced pressure
  2. temperaturethe mixture was heated at 180° C. in a Dean-Stark apparatus for 3 h
  3. temperatureAfter cooling to room temperature
  4. customthe mixture was evaporated to dryness under reduced pressure
  5. customThe residue was triturated with 25 ml of diethyl ether/pentane (1:1)
  6. filtrationThe solid was filtered off
  7. washrinsed with cyclohexane
  8. dissolutiondissolved in 75 ml of DCM
  9. dry with materialThe solution was dried with magnesium sulfate
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-4a38a2672334485fb2cce25f11166507
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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