Carbamic acid, N-methyl-, ethyl ester → 3-Methoxy-4-methylaniline

HRID 1580318Notes

Reaction equation

HRID 1580318 reaction equation
CNC(OCC)=O.[CH3:8][O:9][CH:10]1[CH:15]([CH3:16])[CH2:14][CH2:13][CH:12]([NH2:17])[CH2:11]1.C([O-])(=O)C>O1CCOCC1>[CH3:8][O:9][C:10]1[CH:11]=[C:12]([CH:13]=[CH:14][C:15]=1[CH3:16])[NH2:17]

Participants

4

Reactant 2

HCID 7752Carbamic acid, N-methyl-, ethyl esterHCID 86732944HCID 86732944, compound

Product 1

HCID 278823-Methoxy-4-methylaniline

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

4.2 g of N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-methyl-urethane (melting point 189°- 191°C) are suspended in 50 ml of dioxane and dissolved in 50 ml dioxane after addition of 2 g of 3-methoxy-4-methyl-cyclohexyl-amine-acetate (melting point 134° - 136° C) (obtained by hydrogenation of the nucleus of 3-methoxy-4-methylaniline at Co2O3 at 260°C and under a pressure of 250 atmospheres H2) and heated for about 1 hour to 110°C, in which process the methanol which has formed during the reaction is distilled off. After cooling, water is added and the N-[4-(β-<2-methoxy-5-chlorobenzamido>-ethyl)-benzenesulfonyl]-N'-(3-methoxy-4-methylcyclohexyl)-urea precipitates in crystalline form and it is recrystallized from methanol (melting point 179° - 181° C). In analogous manner, there is obtained: from N-[4-(β-<3-trifluoromethylbenzamido>-ethyl)-benzenesulfonyl]-methylurethane (melting point 178° - 180°C)

Sources & evidence

ORD record
ord-c9c503a224b146d8937b532d9c7284d0
Source dataset
uspto-grants-1976_01
Patent number
US03932503

Reaction notes

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