Sodium Hydroxide → 4-(1-Carbamoyl-cyclohexylamino)benzoic acid ethyl ester

HRID 1966953Notes

Reaction equation

HRID 1966953 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2([C:18]#[N:19])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][CH:6]=1)[CH3:2].[OH-:21].[Na+]>S(=O)(=O)(O)O>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2([C:18](=[O:21])[NH2:19])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)=[CH:7][CH:6]=1)[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 666186724-(1-Cyano-cyclohexylamino)benzoic acid ethyl ester

Product 1

HCID 666185994-(1-Carbamoyl-cyclohexylamino)benzoic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

550 mg (2.02 mmol) of 4-(1-cyanocyclohexylamino)-benzoic acid ethyl ester are dissolved in 20 ml of concentrated sulfuric acid. The reaction medium is stirred at room temperature for 5 hours. The reaction medium is poured gently onto ice, the pH is brought to 12 with sodium hydroxide, and the resulting mixture is extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated off. The product is chromatographed on silica gel (60/40 heptane/ethyl acetate). The product 4-(1-carbamoyl-cyclohexylamino)benzoic acid ethyl ester is obtained in the form of a white solid.

Workup

  1. additionThe reaction medium is poured gently onto ice
  2. extractionthe resulting mixture is extracted with ethyl acetate
  3. washwashed with water
  4. dry with materialThey are dried over sodium sulfate
  5. customThe solvents are evaporated off
  6. customThe product is chromatographed on silica gel (60/40 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-94fc042d51be4679bee0ba184cf6dcdb
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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