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

HRID 520984Notes

Reaction equation

HRID 520984 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-a18d776c880d49c5a18c05ae2c782394
Source dataset
uspto-grants-2016_05
Patent number
US09328067B2

Reaction notes

Loading…