4-Chlorobenzoyl chloride → 4-[p-chloro-N-(6-methoxybiphenyl-3-yl)-benzamido]butyric acid

HRID 1389226Notes

Reaction equation

HRID 1389226 reaction equation
[CH3:1][O:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:7][C:6]([NH:15][CH2:16][CH2:17][CH2:18][C:19]([O:21]CC)=[O:20])=[CH:5][CH:4]=1.C(N(C(C)C)C(C)C)C.[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38](Cl)=[O:39])=[CH:36][CH:35]=1.[OH-].[K+]>C1C=CC=CC=1.C(O)C>[Cl:33][C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:15]([CH2:16][CH2:17][CH2:18][C:19]([OH:21])=[O:20])[C:6]2[CH:7]=[C:8]([C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=3)[C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[O:39])=[CH:36][CH:35]=1

Participants

7

Reactant 4

HCID 85014-Chlorobenzoyl chlorideHCID 14797Potassium HydroxideHCID 81531DiisopropylethylamineHCID 20298363Ethyl 4-(6-methoxybiphenyl-3-yl)aminobutyrate

Product 1

HCID 202983854-[p-chloro-N-(6-methoxybiphenyl-3-yl)-benzamido]butyric acidYield 74.9%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolvent2×HCID 702EthanolSolvent

Procedure

8.0 g of ethyl 4-(6-methoxybiphenyl-3-yl)aminobutyrate and, 3.3 g of ethyldiisopropylamine in 50 ml of benzene are reacted, analogously to Example 47b), with 4.6 g of p-chlorobenzoyl chloride. The reaction product is dissolved in 50 ml of benzene and, after the addition thereto of a solution of 2.3 g of potassium hydroxide in 20 ml of ethanol, is then stirred for 8 hours at room temperature. After distilling off the solvent, the residue is dissolved in water; the resulting solution is acidified with dilute hydrochloric acid and extracted with diethyl ether. The residue (remaining after evaporating off the ether) is recrystallized from ethyl acetate/petrol ether (1:1) to obtain 8.1 g (73.5% of theory) of 4-[p-chloro-N-(6-methoxybiphenyl-3-yl)-benzamido]butyric acid, MP 114° to 116°.

Workup

  1. additionafter the addition
  2. distillationAfter distilling off the solvent
  3. dissolutionthe residue is dissolved in water
  4. extractionextracted with diethyl ether
  5. customafter evaporating off the ether)
  6. customis recrystallized from ethyl acetate/petrol ether (1:1)

Sources & evidence

ORD record
ord-0a6bdbb4d5554476bd64ffff8e6ae889
Source dataset
uspto-grants-1981_01
Patent number
US04243678

Reaction notes

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