Thionyl Chloride → Methyl 2-(dimethylamino)-N-[[[[[(diethoxyphosphinothioyl)cyclopentylamino]sulfinyl]methylamino]carbonyl]oxy]-2-oxoethanimidothioate

HRID 647797Notes

Reaction equation

HRID 647797 reaction equation
[CH3:1][N:2]([CH3:14])[C:3](=[O:13])[C:4]([S:11][CH3:12])=[N:5][O:6][C:7]([NH:9][CH3:10])=[O:8].[S:15](Cl)(Cl)=[O:16].[CH:19]1([NH:24][P:25](=[S:32])([O:29][CH2:30][CH3:31])[O:26][CH2:27][CH3:28])[CH2:23][CH2:22][CH2:21][CH2:20]1>N1C=CC=CC=1>[CH3:14][N:2]([CH3:1])[C:3](=[O:13])[C:4]([S:11][CH3:12])=[N:5][O:6][C:7]([NH:9][CH2:10][S:15]([N:24]([P:25]([O:29][CH2:30][CH3:31])([O:26][CH2:27][CH3:28])=[S:32])[CH:19]1[CH2:20][CH2:21][CH2:22][CH2:23]1)=[O:16])=[O:8]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 31657OxamylHCID 20483188O,O-diethyl cyclopentylphosphoramidothioate

Product 1

HCID 86739082Methyl 2-(dimethylamino)-N-[[[[[(diethoxyphosphinothioyl)cyclopentylamino]sulfinyl]methylamino]carbonyl]oxy]-2-oxoethanimidothioate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 2-(dimethylamino)-N-[[[[[(diethoxyphosphinothioyl)cyclopentylamino]sulfinyl]methylamino]carbonyl]oxy]-2-oxoethanimidothioate was prepared by the procedure employed in Example 21, by reacting methyl 2-(dimethylamino)-N-[[(methylamino)carbonyl]oxy]-2-oxoethanimidothioate (3.29 g, 0.015 mole), thionyl chloride (1.79 g, 0.015 mole), and O,O-diethyl cyclopentylphosphoramidothioate (3.56 g, 0.015 mole) in pyridine (10 ml). Column chromatography afforded 2.5 g of an oil of the formula below, nD24 : 1.5322. ##STR43##

Sources & evidence

ORD record
ord-9f0e32e3b13a4b779361d15305154456
Source dataset
uspto-grants-1983_10
Patent number
US04410518

Reaction notes

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