Diethyl Ether → 1-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid

HRID 1851834Notes

Reaction equation

HRID 1851834 reaction equation
[OH-].[Na+].C1(C[O:10][C:11]([C:13]2([NH:19][C:20]([C:22]3[S:23][C:24]4[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=4[CH:26]=3)=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])C=CC=CC=1.CCOCC>O1CCCC1>[S:23]1[C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[CH:26]=[C:22]1[C:20]([NH:19][C:13]1([C:11]([OH:12])=[O:10])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)=[O:21]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 576728971-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester

Product 1

HCID 432420401-[(2-Benzothienylcarbonyl)amino]cyclohexanecarboxylic acidYield 83.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

42 ml of 2N sodium hydroxide aqueous solution was added to a solution of 10 g (24 mmol) of 1-[(2-benzothienylcarbonyl)amino]cyclohexanecarboxylic acid phenylmethyl ester in 20 ml of tetrahydrofuran, and the mixture was refluxed under heating for 3 days. After ether was added to the reaction solution to wash it, the aqueous layer was neutralized by concentrated hydrochloric acid, and the precipitated crystal was collected by filtration. The obtained crystal was dried under reduced pressure to give 6.1 g (80%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 days
  3. washto wash it
  4. filtrationthe precipitated crystal was collected by filtration
  5. customThe obtained crystal was dried under reduced pressure

Sources & evidence

ORD record
ord-65e4f614dded4f4ea76851677edc94d5
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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