Hydrochloric Acid → HCID 178517435, compound

HRID 1022404Notes

Reaction equation

HRID 1022404 reaction equation
[C:1]1([Mg]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:9][C:10]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:11]=1[C:12]#[N:13].[C:19](Cl)(=O)[O:20]C.Cl.C(=O)(O)[O-].[Na+]>C1COCC1.CC(OC)(C)C>[Cl:18][C:17]1[CH:16]=[CH:15][CH:14]=[C:11]2[C:10]=1[NH:9][C:19](=[O:20])[N:13]=[C:12]2[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 126273632-Amino-3-chlorobenzonitrileHCID 178418255HCID 178418255, compound

Product 1

HCID 178517435HCID 178517435, compoundYield 81.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

To 7.10 g of phenylmagnesium bromide (32% THF solution) was added dropwise a solution of 953 mg of 2-amino-3-chlorobenzonitrile in THF (7 ml) at room temperature, followed by heating under reflux for 30 minutes. To the resulting reaction product was added dropwise 885 mg of methyl chlorocarbonate under ice cooling, followed by heating under reflux for 40 minutes. The resulting reaction solution was cooled and poured into 40 ml of 2N-hydrochloric acid, and 8 g of sodium bicarbonate and 20 ml of MTBE were added thereto, followed by stirring. Precipitated crystals were collected by filtration to obtain 1.30 g of the titled compound. 1H NMR (DMSO-d6): 7.24(1H, t, J=8.0 Hz), 7.57-7.70 (6H, m), 7.90-7.93 (1H, m), 11.45 (br. s).

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 30 minutes
  3. customTo the resulting reaction product
  4. temperatureby heating
  5. temperatureunder reflux for 40 minutes
  6. customThe resulting reaction solution
  7. temperaturewas cooled
  8. additionwere added
  9. customPrecipitated crystals
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-15f80f6552c94fe485bd93744126c5a9
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

Loading…