DE293163A - - Google Patents
Info
- Publication number
- DE293163A DE293163A DE293163A DE 293163 A DE293163 A DE 293163A DE 293163 A DE293163 A DE 293163A
- Authority
- DE
- Germany
- Prior art keywords
- acids
- barbituric
- acid
- derivatives
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 15
- 150000007656 barbituric acids Chemical class 0.000 claims description 14
- -1 isopropyl monosubstituted malonic acids Chemical class 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 5
- 238000009835 boiling Methods 0.000 claims description 5
- NDEMNVPZDAFUKN-UHFFFAOYSA-N guanidine;nitric acid Chemical compound NC(N)=N.O[N+]([O-])=O.O[N+]([O-])=O NDEMNVPZDAFUKN-UHFFFAOYSA-N 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 5
- 230000008018 melting Effects 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- 239000004202 carbamide Substances 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002691 malonic acids Chemical class 0.000 claims description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 239000000155 melt Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims 3
- 239000013067 intermediate product Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- SWKHEIHSYWZUJP-UHFFFAOYSA-N 1,3-diazinane-2,4,6-trione Chemical class O=C1CC(=O)NC(=O)N1.O=C1CC(=O)NC(=O)N1 SWKHEIHSYWZUJP-UHFFFAOYSA-N 0.000 claims 1
- UMNUSSWRSRDUIL-UHFFFAOYSA-N 5-benzyl-5-propan-2-yl-1,3-diazinane-2,4,6-trione Chemical compound C=1C=CC=CC=1CC1(C(C)C)C(=O)NC(=O)NC1=O UMNUSSWRSRDUIL-UHFFFAOYSA-N 0.000 claims 1
- MCOQHIWZJUDQIC-UHFFFAOYSA-N barban Chemical compound ClCC#CCOC(=O)NC1=CC=CC(Cl)=C1 MCOQHIWZJUDQIC-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 230000004048 modification Effects 0.000 claims 1
- 238000012986 modification Methods 0.000 claims 1
- 150000002148 esters Chemical class 0.000 description 5
- KJUMEJFSCGIBQA-UHFFFAOYSA-N 5-(2-cyclohexylethyl)-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1CCC1CCCCC1 KJUMEJFSCGIBQA-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- 230000000147 hypnotic effect Effects 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
- RATSVJLVTJDKSI-UHFFFAOYSA-N 5-cyclohexyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1NC(=O)NC(=O)C1C1CCCCC1 RATSVJLVTJDKSI-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 238000010626 work up procedure Methods 0.000 description 2
- VTCZQZWNJYMGGM-UHFFFAOYSA-N 2-cyano-2-propan-2-ylpentanoic acid Chemical compound CCCC(C#N)(C(C)C)C(O)=O VTCZQZWNJYMGGM-UHFFFAOYSA-N 0.000 description 1
- WYPYCIKNBNGGII-UHFFFAOYSA-N 2-cyclohexylpropanedioic acid Chemical class OC(=O)C(C(O)=O)C1CCCCC1 WYPYCIKNBNGGII-UHFFFAOYSA-N 0.000 description 1
- PLFBWOPHLBPGEJ-UHFFFAOYSA-N 2-ethyl-2-propan-2-ylpropanedioic acid Chemical class CCC(C(C)C)(C(O)=O)C(O)=O PLFBWOPHLBPGEJ-UHFFFAOYSA-N 0.000 description 1
- JSVFGUVEXOEQEC-UHFFFAOYSA-N 5-imino-1,3-diazinane-2,4,6-trione Chemical class N=C1C(=O)NC(=O)NC1=O JSVFGUVEXOEQEC-UHFFFAOYSA-N 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 230000006203 ethylation Effects 0.000 description 1
- 238000006200 ethylation reaction Methods 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DDBREPKUVSBGFI-UHFFFAOYSA-N phenobarbital Chemical compound C=1C=CC=CC=1C1(CC)C(=O)NC(=O)NC1=O DDBREPKUVSBGFI-UHFFFAOYSA-N 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- HHLXJTDUHFBYAU-UHFFFAOYSA-N probarbital Chemical compound CCC1(C(C)C)C(=O)NC(=O)NC1=O HHLXJTDUHFBYAU-UHFFFAOYSA-N 0.000 description 1
- GHPCKDRAHKFQBY-UHFFFAOYSA-N propan-2-yl 2-cyanoacetate;sodium Chemical compound [Na].CC(C)OC(=O)CC#N GHPCKDRAHKFQBY-UHFFFAOYSA-N 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
Family
ID=
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