Ammonium Chloride → Methyl 2-(((2-amino-5-chlorophenyl)thio)methyl)benzoate

HRID 70476Notes

Reaction equation

HRID 70476 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N+:20]([O-])=O)=[C:6]([S:8][CH2:9][C:10]2[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=2[C:12]([O:14][CH3:15])=[O:13])[CH:7]=1.[NH4+].[Cl-]>CO.C1COCC1.[Zn]>[NH2:20][C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][C:6]=1[S:8][CH2:9][C:10]1[CH:19]=[CH:18][CH:17]=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 2

HCID 25517Ammonium ChlorideHCID 86691004Methyl 2-(((5-chloro-2-nitrophenyl)thio)methyl)benzoate

Product 1

HCID 82976200Methyl 2-(((2-amino-5-chlorophenyl)thio)methyl)benzoateYield 106.9%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Following General Procedure L, the title compound (158 mg, crude) was prepared from methyl 2-(((5-chloro-2-nitrophenyl)thio)methyl)benzoate (163 mg, 0.48 mmol), Zn (780 mg, 12.0 mmol) and saturated aqueous NH4Cl (10 ml) in MeOH (5 ml) and THF (5 ml). The crude product was used in the next reaction without further purification.

Sources & evidence

ORD record
ord-41d3c4c447d94109bddb2911759b3814
Source dataset
uspto-grants-2014_09
Patent number
US08822530B2

Reaction notes

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