Water → HCID 68630895, compound

HRID 1945177Notes

Reaction equation

HRID 1945177 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]2([C:14]#[N:15])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:4][CH:3]=1.[OH2:16]>S(=O)(=O)(O)O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2([C:14]([NH2:15])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 962WaterHCID 68631576HCID 68631576, compound

Product 1

HCID 68630895HCID 68630895, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

4.2 g (13.4 mmol) of 1-(4-iodophenyl-amino)-cyclopentanecarbonitrile are dissolved in 40 ml of concentrated sulfuric acid. The reaction medium is stirred for 48 hrs at ambient temperature, then it is poured gently into water and the pH is adjusted to 7 with soda and [the mixture] extracted with ethyl acetate. The organic phases are combined and washed with water. They are dried over sodium sulfate. The solvents are evaporated and the residue is crystallized in a little dichloromethane and heptane. It is then filtered and dried. 4.2 g of 1-(4-iodophenylamino)-cyclopentanecarboxamide are obtained in the form of a pink solid. (M.Pt.=148° C., Yield=94%).

Workup

  1. extraction[the mixture] extracted with ethyl acetate
  2. washwashed with water
  3. dry with materialThey are dried over sodium sulfate
  4. customThe solvents are evaporated
  5. customthe residue is crystallized in a little dichloromethane and heptane
  6. filtrationIt is then filtered
  7. customdried

Sources & evidence

ORD record
ord-05120531f62548639dfa54b80ed1c2ac
Source dataset
uspto-grants-2013_03
Patent number
US08394990B2

Reaction notes

Loading…