Hydrochloric Acid → HCID 66681061, compound

HRID 1966958Notes

Reaction equation

HRID 1966958 reaction equation
[O-:1][C:2]#N.[K+].[I:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13]2([C:19]#[N:20])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[CH:8][CH:7]=1.Cl.[OH2:22]>C(O)(=O)C>[I:5][C:6]1[CH:7]=[CH:8][C:9]([N:12]2[C:13]3([CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]3)[C:19](=[O:22])[NH:20][C:2]2=[O:1])=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 11378442Potassium cyanateHCID 66618606HCID 66618606, compound

Product 1

HCID 66681061HCID 66681061, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
60 °C

Procedure

1.8 g (22.2 mmol, 2 eq.) of potassium cyanate are added at 30° C. to a solution of 3.7 g (11.3 mmol, 1 eq.) of 1-(4-iodophenylamino)cyclohexanecarbonitrile in 30 ml of glacial acetic acid. The reaction medium is stirred at 60° C. overnight. 5 ml of hydrochloric acid and then 3 ml of water are added. The medium is heated at 90° C. for 1 hour and then at room temperature for 3 hours. Water is then poured into the reaction medium, and the precipitate formed is filtered off and then chromatographed on silica gel (50/50 heptane/ethyl acetate). 180 mg of 1-(4-iodophenyl)-1,3-diaza-spiro[4.5]decane-2,4-dione are obtained in the form of an orange-coloured solid.

Workup

  1. temperatureThe medium is heated at 90° C. for 1 hour
  2. waitat room temperature for 3 hours
  3. customthe precipitate formed
  4. filtrationis filtered off
  5. customchromatographed on silica gel (50/50 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-f85e1becdb1641de82cca07c27ceff52
Source dataset
uspto-grants-2013_04
Patent number
US08420682B2

Reaction notes

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