Methyl iodide → N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline

HRID 1111266Notes

Reaction equation

HRID 1111266 reaction equation
[OH-].[Na+].Cl.[NH2:4][CH2:5][CH2:6][SH:7].[CH3:8]I.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1>O.C(N(CC)CC)C>[N+:17]([C:14]1[CH:15]=[CH:16][C:11]([NH:4][CH2:5][CH2:6][S:7][CH3:8])=[CH:12][CH:13]=1)([O-:19])=[O:18]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 9082Cysteamine HydrochlorideHCID 9590p-FluoronitrobenzeneHCID 14798Sodium Hydroxide

Product 1

HCID 14646022N-[2-(Methylsulfanyl)ethyl]-4-nitroaniline

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8471TriethylamineSolvent

Conditions

Temperature
40 °C

Procedure

A solution of 0.4 mole of sodium hydroxide in 100 ml of water is added dropwise at 30° C. to a solution of 0.4 mole (45.4 g) of 2-aminoethanethiol hydrochloride and 0.4 mole (56.8 g) of methyl iodide in 100 ml of water. After a further hour of stirring at 40° C., 0.15 mole (21.2 g) of 4-fluoronitrobenzene and 42 ml of triethylamine are added.

Sources & evidence

ORD record
ord-1544e2f0c9ce450da58d7dc868bc2317
Source dataset
uspto-grants-1990_12
Patent number
US04979961

Reaction notes

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