Chloride → 4-Chlorophenyl 4-(8-cyclohexyloctylamino)benzoate

HRID 903412Notes

Reaction equation

HRID 903412 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(N(CC)CC)C.[Cl-].Cl.[CH:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37](Cl)=[O:38])=[CH:35][CH:34]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1>C(Cl)Cl>[CH:18]1([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][NH:32][C:33]2[CH:41]=[CH:40][C:36]([C:37]([O:8][C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)=[O:38])=[CH:35][CH:34]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 312ChlorideHCID 46844-ChlorophenolHCID 8471TriethylamineHCID 20475769p-(8-Cyclohexyloctyl)aminobenzoyl chloride hydrochloride

Product 1

HCID 204758364-Chlorophenyl 4-(8-cyclohexyloctylamino)benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 6.4 g. 4-chlorophenol and 7.6 g. triethylamine in 500 ml. meythlene chloride is added 10.4 g. 4-(8-cyclohexyloctylamino)benzoyl chloride hydrochloride in 250 ml. methylene chloride. After four hours at reflux, the solution is cooled, washed with water and dilute phosphoric acid, and dried. After passing the solution through a column of alumina, the solvent is evaporated an the residue is crystallized from diisopropyl ether.

Workup

  1. temperatureAfter four hours at reflux
  2. temperaturethe solution is cooled
  3. washwashed with water and dilute phosphoric acid
  4. customdried
  5. customthe solvent is evaporated an the residue
  6. customis crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-3940520d066b43778c8bea81293339ff
Source dataset
uspto-grants-1980_10
Patent number
US04227014

Reaction notes

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