Hydrochloric Acid → HCID 19098340, compound

HRID 1975729Notes

Reaction equation

HRID 1975729 reaction equation
Cl.[Cl:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C(OCC)C.Cl.[N:25]([O-])=[O:26].[Na+]>O>[N:25]([N:8]([CH2:7][C:6]1[CH:17]=[CH:18][C:3]([Cl:2])=[CH:4][CH:5]=1)[C:9]1[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=1)=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 19098337HCID 19098337, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19098340HCID 19098340, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of N-(4-chlorobenzyl)-4-methoxyaniline hydrochloride salt (141.4 g; 497.5 mmol), prepared as above, in 1500 mL water, 750 mL diethyl ether, and 525 mL aqueous 1N HCl was treated with a solution of sodium nitrite (37.7 g; 547 mmol) in 150 mL water. After stirring for 2 hours at ambient temperature the reaction mixture was extracted twice with diethyl ether. The combined extracts were washed with water, dried over magnesium sulfate, and concentrated to give N-nitroso-N-(4-chlorobenzyl)-4-methoxyaniline as a yellow solid.

Workup

  1. extractionwas extracted twice with diethyl ether
  2. washThe combined extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-781ee121033945d1ad94a4bd6ba6e69a
Source dataset
uspto-grants-1994_02
Patent number
US05288743

Reaction notes

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