Hydrochloric Acid → HCID 58268035, compound

HRID 1898238Notes

Reaction equation

HRID 1898238 reaction equation
[S:1](=[O:3])=[O:2].[Cl:4][C:5]1[CH:10]=[CH:9][C:8](N)=[CH:7][C:6]=1[CH2:12][CH3:13].N([O-])=O.[Na+].[ClH:18]>C(O)(=O)C.O.[Cu]Cl>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([S:1]([Cl:18])(=[O:3])=[O:2])=[CH:7][C:6]=1[CH2:12][CH3:13]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 2071434793-49-2HCID 23668193Sodium Nitrite

Product 1

HCID 58268035HCID 58268035, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Amounts used: 25 mL of acetic acid was saturated with sulfur dioxide, 700 mg of copper(I) chloride, 4.40 g (28.3 mmol) of 4-chloro-3-ethyl-phenylamine dissolved in a mixture of 9 mL of acetic acid and 9 mL of concentrated hydrochloric acid, 2.20 g of sodium nitrite in 10 mL of water. Flash chromatography on silica using 0-20% ethyl acetate in hexanes afforded 3.4 g of the product as a white solid. LC-MSD spectrum not observed;

Sources & evidence

ORD record
ord-e92bacd7699e463490dd48fec6063a83
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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