Hydrochloric Acid → HCID 22314759, compound

HRID 1634037Notes

Reaction equation

HRID 1634037 reaction equation
Br[C:2]1[CH:8]=[C:7]([CH2:9][CH3:10])[C:5](N)=[C:4]([CH2:11][CH3:12])[CH:3]=1.Cl.N([O-])=O.[Na+].[OH:18][PH2]=O.[CH3:21][CH2:22][OH:23]>O.C(O)(=O)C>[CH2:11]([C:4]1[CH:3]=[C:2]([CH2:21][C:22]([OH:18])=[O:23])[CH:8]=[C:7]([CH2:9][CH3:10])[CH:5]=1)[CH3:12]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 6114524-Bromo-2,6-diethylanilineHCID 4124402Phosphinic AcidHCID 23668193Sodium Nitrite

Product 1

HCID 22314759HCID 22314759, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
-5 °C

Procedure

A mixture of 20 g of 4-bromo-2,6-diethylaniline, 160 ml of acetic acid, 100 ml of a concentrated HCl solution, 30 ml of water and 100 ml of EtOH is cooled to −5° C., a solution of 6.6 g of sodium nitrite in 25 ml of water is added dropwise and the mixture is left stirring for 30 minutes at RT. The reaction mixture is poured over 170 ml of 50% H3PO2 cooled to 0° C., the mixture is left stirring for 2 hours at 0° C. and then for 48 hours at RT. The reaction mixture is extracted with ether, the organic phase washed with water, with a 1N NaOH solution, with water, dried over Na2SO4 and the solvent evaporated off under vacuum. The residue is chromatographed on silica gel, eluting with cyclohexane. 18 g of the expected product are obtained.

Workup

  1. waitthe mixture is left
  2. temperaturecooled to 0° C.
  3. waitthe mixture is left
  4. stirringstirring for 2 hours at 0° C.
  5. waitfor 48 hours at RT
  6. extractionThe reaction mixture is extracted with ether
  7. washthe organic phase washed with water, with a 1N NaOH solution, with water
  8. dry with materialdried over Na2SO4
  9. customthe solvent evaporated off under vacuum
  10. customThe residue is chromatographed on silica gel
  11. washeluting with cyclohexane

Sources & evidence

ORD record
ord-3d4dec337b08461fa7ab6d8c09fe7d5c
Source dataset
uspto-grants-2003_01
Patent number
US06506750B1

Reaction notes

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