Ethyl 3-(cyanomethyl)benzoate → Ethyl 3-(2-amino-2-thioxoethyl)benzoate

HRID 1257448Notes

Reaction equation

HRID 1257448 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])#[N:2].C(OCC)(=O)C.Cl.P([S-])(OCC)(OCC)=[S:23]>>[NH2:2][C:1](=[S:23])[CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[CH:13][CH:14]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 3

HCID 83311Ethyl 3-(cyanomethyl)benzoateHCID 1385274Diethyl dithiophosphate, potassium saltHCID 21866389Hydrogen chloride-ethyl acetate

Product 1

HCID 58127520Ethyl 3-(2-amino-2-thioxoethyl)benzoateYield 79%

Procedure

By a method similar to that in Example 178a and using the compound (4.23 g, 22.4 mmol) obtained in Example 180a, 4M hydrogen chloride-ethyl acetate solution (42 mL) and O,O-diethyl dithiophosphate (4.50 mL, 26.8 mmol), the title compound (3.94 g, 79%) was obtained as colorless crystals.

Sources & evidence

ORD record
ord-4666f35883284338bbe37402d3b8c5ea
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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