2-Thiocresol → N-methyl-3-[(2-methylphenyl)thio]benzenepropanamine

HRID 1199720Notes

Reaction equation

HRID 1199720 reaction equation
Cl.[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9](Cl)[CH:8]=1.[OH-].[Na+].[CH3:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[SH:23]>>[CH3:2][NH:3][CH2:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([S:23][C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:16])[CH:8]=1

Participants

4

Reactant 3

HCID 87122-ThiocresolHCID 14798Sodium Hydroxide2×HCID 22293947N-Methyl-3-chloro-benzenepropanamine hydrochloride

Product 1

HCID 9919103N-methyl-3-[(2-methylphenyl)thio]benzenepropanamine

Procedure

N-Methyl-3-chloro-benzenepropanamine hydrochloride (13.14 g, 0.06 mol), 25%, by weight, sodium hydroxide solution (9.6 g of solution; 0.06 mol of sodium hydroxide), sodium hydroxide pellets (2.0 g, 0.05 mol) and 2-methylbenzenethiol (6.2 g, 0.05 mol) were reacted to provide N-methyl-3-[(2-methylphenyl)thio]benzenepropanamine as an oil. The oil was purified by preparative HPLC and then converted to the hydrochloride salt as in Example 1. Recrystallization from methylene chlorideethyl acetate provided approximately 3.0 g of title compound. m.p. ≈90° C.

Sources & evidence

ORD record
ord-530a845edaa742b3b930b809d8fd61c9
Source dataset
uspto-grants-1990_02
Patent number
US04902710

Reaction notes

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