Claims
- 1. A process for the manufacture of a 4-substituted oxazolinone-(5) compound of the formula ##STR3## wherein R.sup.1 is phenyl which may be unsubstituted or substituted by chlorine, bromine, nitro, methoxy, dimethoxy, methyl or ethyl, and
- R.sup.2 is hydrogen, methyl or benzyl which is substituted by one or more hydroxy, alkoxy, acetoxy, trifluoromethyl, halogen or methyl, and
- R.sup.3 is an alkyl of 1 to 4 carbons, --CH.sub.2 OH, --CH(OH)CH.sub.3, --CH.sub.2 SH, --CH.sub.2 CH.sub.2 SCH.sub.3, --CH.sub.2 CO.sub.2 H, --CH.sub.2 CH.sub.2 CO.sub.2 H, --CH.sub.2 --(CH.sub.2).sub.2 --NH.sub.2, --CH.sub.2 --(CH.sub.2).sub.3 --NH.sub.2, --CH.sub.2 CH.sub.2 CH(OH)CH.sub.2 NH.sub.2, ##STR4## which consists essentially of reacting an oxazolinone-(5) compound of the formula ##STR5## wherein R.sup.1 and R.sup.2 are defined above, with a compound of the formula R.sup.3 X where R.sup.3 is defined above and X is bromine, chlorine or iodine in an anhydrous aprotic solvent in the presence of a tertiary amine selected from the group consisting of triethylamine, ethyldiisopropylamine, a Hunig's base, N,N-dimethyl-cyclohexylamine, pyridine and a picoline at temperatures of from about -10.degree. C. to 100.degree. C., whereby the oxazolinone-(5) compound is substituted in the 4-position, with the proviso that when R.sup.2 is substituted benzyl, then R.sup.3 can only be an alkyl of 1 to 4 carbons; when R.sup.2 is hydrogen and R.sup.3 is an alkyl of 1 to 4 carbons, then of said alkyl R.sup.3 can only be --CH.sub.3, --CH(CH.sub.3).sub.2, --CH(CH.sub.3)CH.sub.2 CH.sub.3 or --CH.sub.2 CH(CH.sub.3).sub.2, otherwise R.sub.3 can be any of the above shown substituents; and, when R.sup.2 is methyl, then R.sup.3 can only be ##STR6##
- 2. The process of claim 1 wherein said aprotic solvent is dimethylformamide, dimethylsulfoxide, hexamethylphosphoric acid triamide, methylene chloride, benzene or tetrahydrofuran.
- 3. The process of claim 1 wherein said tertiary amine is ethyldiisopropylamine.
- 4. The process of claim 1 wherein R.sup.2 is hydrogen, R.sup.3 is ##STR7## and X is chlorine or iodine.
- 5. The process of claim 1 wherein R.sup.2 is hydrogen, R.sup.3 is --CH.sub.2 CO.sub.2 H and X is chlorine.
- 6. The process of claim 1 wherein R.sup.2 is methyl, R.sup.3 is ##STR8## and X is chlorine.
- 7. The process of claim 1 wherein R.sup.2 is 3,4-dimethoxybenzyl or 3,4-dihydroxybenzyl and R.sup.3 is methyl.
Priority Claims (1)
Number |
Date |
Country |
Kind |
2336718 |
Jul 1973 |
DEX |
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Parent Case Info
This is a continuation of application Ser. No. 891,456, filed Mar. 29, 1978, now U.S. Pat. No. 4,264,771, which is a continuation of Ser. No. 484,068, filed July 16, 1974, now abandoned.
US Referenced Citations (2)
Number |
Name |
Date |
Kind |
3676453 |
Pines et al. |
Jul 1972 |
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4264771 |
Stealich et al. |
Apr 1981 |
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Continuations (2)
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Number |
Date |
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Parent |
891456 |
Mar 1978 |
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Parent |
484068 |
Jul 1974 |
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