Dicyclohexylamine → HCID 19762694, compound

HRID 1651321Notes

Reaction equation

HRID 1651321 reaction equation
[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:11](O)=[O:12])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.C1(NC2CCCCC2)CCCCC1.S(Cl)([Cl:34])=O>ClCCl>[CH3:1][C:2]1([C:8]2[CH:9]=[C:10]([CH:14]=[CH:15][C:16]=2[O:17][CH3:18])[C:11]([Cl:34])=[O:12])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 7582DicyclohexylamineHCID 24386Thionyl ChlorideHCID 18371174HCID 18371174, compound

Product 1

HCID 19762694HCID 19762694, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a round bottom flask, there are introduced 4.96 g (20 mmoles) of 3-(1-methylcyclohexyl)-4-methoxy benzoic acid, 75 ml of dichloromethane, and 4 ml (20 mmoles) of dicyclohexylamine. The reaction mixture is stirred for 1 hour. To the resulting solution, there are added 1.45 ml (20 mmoles) of thionyl chloride (SOCl2) and the mixture is stirred for 2 hours at ambient temperature. The reaction mixture is then evaporated to dryness and taken up in 200 ml of ether. The dicyclohexyl-ammonium chloride is filtered off and the solvent is evaporated, yielding 5.30 g (100% yield) of crude 3-(1-methylcyclohexyl)-4-methoxy benzoyl chloride which is used, as is, for the following synthesis:

Workup

  1. stirringthe mixture is stirred for 2 hours at ambient temperature
  2. customThe reaction mixture is then evaporated to dryness
  3. filtrationThe dicyclohexyl-ammonium chloride is filtered off
  4. customthe solvent is evaporated

Sources & evidence

ORD record
ord-b20024e73283474e853e0412295461c0
Source dataset
uspto-grants-1990_05
Patent number
US04927928

Reaction notes

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