Hydrochloric Acid → HCID 11321809, compound

HRID 890590Notes

Reaction equation

HRID 890590 reaction equation
C([O-])(C)(C)C.[K+].ClC1C=CC(O[CH2:13][C:14]#[N:15])=CC=1.[N+:18]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[CH:22]=1)([O-:20])=[O:19].Cl>CN(C)C=O.O>[N+:18]([C:21]1[CH:30]=[CH:29][C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]=1[CH2:13][C:14]#[N:15])([O-:20])=[O:19]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 113922-NitronaphthaleneHCID 3064442-(4-Chlorophenoxy)acetonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 11321809HCID 11321809, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Conditions

Temperature
-10 °C

Procedure

Prepare a solution of 53.5 g (0.477 mol) of potassium tert.-butanolate in 400 ml of dimethylformamide. Cool the resulting solution to −10° C. and add thereto, over the course of about 1 hour, a solution of 40 g of 4-chlorophenoxyacetonitrile (0.24 mol) and 37 g of 2-nitronaphthalene (0.213 mol) in 200 ml of dimethylformamide. After 2 hours at −5° C., pour the mixture into 4 litres of water containing 1 litre of concentrated hydrochloric acid and extract the aqueous phase with 3×500 ml of dichloromethane. Wash the organic phase with 300 ml of water, dry it over magnesium sulphate, filter and then evaporate off the solvent.

Workup

  1. additionadd
  2. customover the course of about 1 hour
  3. extractionextract the aqueous phase with 3×500 ml of dichloromethane
  4. washWash the organic phase with 300 ml of water
  5. dry with materialdry it over magnesium sulphate
  6. filtrationfilter
  7. customevaporate off the solvent

Sources & evidence

ORD record
ord-68b656d1096448d29b3dfe8d8bf989cd
Source dataset
uspto-grants-2006_02
Patent number
US06998403B2

Reaction notes

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