4-Amino-4'-chlorodiphenyl → Propynoic acid-(4'-chlorobiphenyl-4-yl)amide

HRID 735018Notes

Reaction equation

HRID 735018 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[C:16]([OH:20])(=O)[C:17]#[CH:18].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([C:28]2[CH:33]=[CH:32][C:31]([NH2:34])=[CH:30][CH:29]=2)=[CH:24][CH:23]=1>ClCCl>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([C:28]2[CH:33]=[CH:32][C:31]([NH:34][C:16](=[O:20])[C:17]#[CH:18])=[CH:30][CH:29]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 86754-Amino-4'-chlorodiphenylHCID 10110Propiolic AcidHCID 10868Dicyclohexylcarbodiimide

Product 1

HCID 86060771Propynoic acid-(4'-chlorobiphenyl-4-yl)amide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

36 mL of a 1 molar DCC solution in dichloromethane is added dropwise at −10° C. to a solution of 4.9 g (70 mmol) of propynoic acid in 120 mL of dichloromethane and the mixture is stirred for 30 minutes. Then 7 g (34.37 mmol) 4′-chlorobiphenyl-4-ylamine, dissolved in dichloromethane, is slowly added dropwise and the mixture is stirred for 2 hours at −8° C. The reaction mixture is then filtered through CELITE®E filter aid, washed again with methanol, and the filtrate is evaporated down. The purification is carried out by column chromatography on silica gel (eluant: cyclohexane/ethyl acetate (6:1 to 2:1)). Yield: 7.6 g (95% of theory); C15H10ClN0 (M=255.70); calc.: molecular ion peak (M+H)+: 256/8 (Cl); found: molecular ion peak (M+H)+: 256/8 (Cl); Rf value: 0.2 (silica gel, cyclohexane/ethyl acetate (1:1)).

Workup

  1. additionis slowly added dropwise
  2. stirringthe mixture is stirred for 2 hours at −8° C
  3. filtrationThe reaction mixture is then filtered through CELITE®E
  4. filtrationfilter aid
  5. washwashed again with methanol
  6. customthe filtrate is evaporated down
  7. customThe purification

Sources & evidence

ORD record
ord-9ebba04921a14452976439eb3eab0f54
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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