Hydrochloric Acid → 98279-07-3

HRID 513369Notes

Reaction equation

HRID 513369 reaction equation
[O:1]=[S:2]([Cl:4])Cl.N[C:6]1[CH:13]=[CH:12][C:9]([C:10]#[N:11])=[CH:8][C:7]=1[N+:14]([O-:16])=[O:15].N([O-])=[O:18].[Na+].Cl>Cl[Cu]>[C:10]([C:9]1[CH:12]=[CH:13][C:6]([S:2]([Cl:4])(=[O:1])=[O:18])=[C:7]([N+:14]([O-:16])=[O:15])[CH:8]=1)#[N:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 5959014-Amino-3-nitrobenzonitrileHCID 23668193Sodium Nitrite

Product 1

HCID 5459493798279-07-3Yield 99.2%

Reagents, catalysts & solvents 1

HCID 62652Cuprous chlorideCatalyst

Procedure

In a similar fashion using route 3a general procedure 10, SOCl2 (2.5 ml, 33.7 mmol), CuCl (30 mg, 0.30 mmol), 4-amino-3-nitrobenzonitrile (1 g, 6.13 mmol), NaNO2 (0.61 g, 8.83 mmol) and conc. HCl (6.2 ml) gave the title compound (1.5 g) which was used in the next step without further purification. The structure was confirmed by 1H NMR.

Sources & evidence

ORD record
ord-695e62e9936442aa88fd8b773b5f8364
Source dataset
uspto-grants-2015_08
Patent number
US09102688B2

Reaction notes

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