Process for the selective preparation of N-substituted 1,4-diami

Details Process for the selective preparation of N-substituted 1,4-diami Process for the selective preparation of N-substituted 1,4-diami

1990-05-07

1992-02-25

Hollrah, Glennon H.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564441, 560 22, 560 23, 560 24, 560 29, 560 30, C07C20914, C07C26904

Patent

active

050915819

ABSTRACT:
The invention relates to a process for the selective preparation of N.sup.4 -substituted 1,4-diamino-2-nitrobenzenes of the general formula I ##STR1## in which R.sub.1 denotes hydrogen, halogen, (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkoxy, it being possible for the carbon atoms to be arranged in straight-chain or branched form, and R.sub.2 represents a radical --COO--CH(A)--CH(B)--D with the meanings A=H, B=H, D=Cl, A=H, B=CH.sub.3, D=Cl, A=H, B=H, D=CH.sub.2 Cl or A=CH.sub.3, B=H and D=Cl (compounds of the general formula Ia) or a radical--CH(X)--CH(Y)--Z with the meanings X=H, Y=H, Z=OH, X=CH.sub.3, Y=H, Z=OH, X=H, Y=H, Z=CH.sub.2 OH or X=H, Y=CH.sub.3 and Z=OH (compounds of the general formula Ib) ##STR2## which is characterized in that 1,4-diamino-2-nitrobenzenes of the general formula II ##STR3## wherein R.sub.1 has the abovementioned meaning, are reacted in a first stage with an approximately equimolar amount of a chloroalkyl chloroformate of the general formula Cl--COO--CH(A)--CH(B)--D, wherein A, B and D have the above-mentioned meanings, in a predominantly aqueous medium which contains--based on the water present--not more than 20 percent by weight of an organic solvent, and preferably in a purely aqueous medium to give carbamates of the general formula Ia and if appropriate these carbamates are converted into compounds of the general formula Ib in a second stage by means of treatment with a base.

REFERENCES:
patent: 4005217 (1977-01-01), Berg et al.
patent: 4125601 (1978-11-01), Bugaut et al.
patent: 4470826 (1984-09-01), Bugaut et al. et al.
patent: 4575378 (1986-03-01), Seidel et al.
R. Adams et al., (I), J. Am. Chem. Soc., "Beta-Arylamino Ethanols", 45, pp. 785-790 (1923).
R. Adams et al. (II), J. Am. Chem. Soc., "Tetrahydro-1,2,3-Oxazones and Substituted Gamma-Amino Propanols", 45, pp. 790-795 (1923).

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