Hydrochloric Acid → HCID 58268146, compound

HRID 1898236Notes

Reaction equation

HRID 1898236 reaction equation
[S:1](=[O:3])=[O:2].[C:4]([C:8]1[CH:9]=[C:10](N)[CH:11]=[CH:12][C:13]=1[Cl:14])([CH3:7])([CH3:6])[CH3:5].N([O-])=O.[Na+].[ClH:20]>C(O)(=O)C.O.[Cu]Cl>[C:4]([C:8]1[CH:9]=[C:10]([S:1]([Cl:20])(=[O:3])=[O:2])[CH:11]=[CH:12][C:13]=1[Cl:14])([CH3:7])([CH3:6])[CH3:5]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 1119Sulfur DioxideHCID 23668193Sodium NitriteHCID 59134962HCID 59134962, compound

Product 1

HCID 58268146HCID 58268146, compound

Reagents, catalysts & solvents 3

HCID 62652Cuprous chlorideCatalystHCID 176Acetic AcidSolvent2×HCID 962WaterSolvent

Procedure

Amounts used: 10 mL of acetic acid was saturated with sulfur dioxide, 220 mg of copper(I) chloride, 1.5 g (8.20 mmol) of 3-tert-butyl-4-chloro-phenylamine dissolved in a mixture of 3 mL of acetic acid and 3 mL of concentrated hydrochloric acid, 0.622 g of sodium nitrite in 3 mL of water. Flash chromatography on silica using 0-15% ethyl acetate in hexanes afforded 0.42 g of the product as a white solid. LC-MSD spectrum not observed.

Sources & evidence

ORD record
ord-71f6827de5eb4d7985128dace62caf2f
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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