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

HRID 448761Notes

Reaction equation

HRID 448761 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 aqueous sodium hydroxide 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 heated under reflux 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 obtain 6.1 g (80%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux 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-b7b27f63603e4f37989673c04afd4358
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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