Dicyclohexylcarbodiimide → 4-(5-Chloro-2-methoxy-anilino-carbonyl-methyl)-4'-hydroxybiphenyl

HRID 596319

Reaction equation

HRID 596319 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([CH2:14][C:15]([OH:17])=O)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH3:18][O:19][C:20]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:21]=1[NH2:22].C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1.O1CCOCC1>[Cl:27][C:24]1[CH:25]=[CH:26][C:20]([O:19][CH3:18])([C:15]([CH2:14][C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:7][CH:6]=3)=[CH:13][CH:12]=2)=[O:17])[CH:21]([CH:23]=1)[NH2:22]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 667635-Chloro-2-methoxyanilineHCID 603371(1,1'-Biphenyl)-4-acetic acid, 4'-hydroxy-

Product 1

HCID 706377284-(5-Chloro-2-methoxy-anilino-carbonyl-methyl)-4'-hydroxybiphenylYield 70%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent3×

Procedure

A solution of 10 gm (44 millimols) of 4-hydroxy-4'-biphenyl-acetic acid (see W. H. Linnell and H. J. Smith, J. Chem. Soc. 1959,557) in a mixture of 33 ml of tetrahydrofuran and 162 ml of absolute dioxane were added at 0° C to a solution of 4.63 gm (29.4 millimols) of 2-methoxy-5-chloroaniline (m.p. 83°-85° C) in 40 ml of absolute dioxane, and the mixed solution was subsequently admixed with a solution of 9.1 gm (44 millimols) of N,N'-dicyclohexyl-carbodiimide in 20 ml of dioxane. After 20 hours of reaction time at 0° C, the dicyclohexylurea was filtered off and the solvent was distilled off. The residue was dissolved in 700 ml of chloroform, the solution was washed several times with 2N hydrochloric acid and water, dried over sodium sulfate, and the organic phase was evaporated in vacuo. The light brown, viscous crude product was purified on a silicagel column with toluene/acetic acid (4:1 ) as the eluant. Yield: 70% of theory; m.p. 165°-168° C.

Workup

  1. customAfter 20 hours of reaction time at 0° C
  2. filtrationthe dicyclohexylurea was filtered off
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in 700 ml of chloroform
  5. washthe solution was washed several times with 2N hydrochloric acid and water
  6. dry with materialdried over sodium sulfate
  7. customthe organic phase was evaporated in vacuo
  8. customThe light brown, viscous crude product was purified on a silicagel column with toluene/acetic acid (4:1 ) as the eluant

Sources & evidence

ORD record
ord-627ff893c6de4ec6ad39336ad49d6e68
Source dataset
uspto-grants-1977_03
Patent number
US04010279

Linked notes

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