US2055608A - Ar. tetrahydro-naphthyl thioureas - Google Patents
Ar. tetrahydro-naphthyl thioureas Download PDFInfo
- Publication number
- US2055608A US2055608A US751283A US75128334A US2055608A US 2055608 A US2055608 A US 2055608A US 751283 A US751283 A US 751283A US 75128334 A US75128334 A US 75128334A US 2055608 A US2055608 A US 2055608A
- Authority
- US
- United States
- Prior art keywords
- tetrahydro
- naphthyl
- thioureas
- thiourea
- 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.)
- Expired - Lifetime
Links
- -1 tetrahydro-naphthyl thioureas Chemical class 0.000 title description 5
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
- JRZGPXSSNPTNMA-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-1-amine Chemical class C1=CC=C2C(N)CCCC2=C1 JRZGPXSSNPTNMA-UHFFFAOYSA-N 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003567 thiocyanates Chemical class 0.000 description 2
- RQTPBLRMULNSNS-UHFFFAOYSA-N 1,2,3,4-tetrahydronaphthalen-2-ylthiourea Chemical compound C1=CC=C2CC(NC(=S)N)CCC2=C1 RQTPBLRMULNSNS-UHFFFAOYSA-N 0.000 description 1
- PIVQQUNOTICCSA-UHFFFAOYSA-N ANTU Chemical compound C1=CC=C2C(NC(=S)N)=CC=CC2=C1 PIVQQUNOTICCSA-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- JCGVEGFEGJLZDW-UHFFFAOYSA-N naphthalen-2-ylthiourea Chemical compound C1=CC=CC2=CC(NC(=S)N)=CC=C21 JCGVEGFEGJLZDW-UHFFFAOYSA-N 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical class [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003585 thioureas Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/16—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline
Definitions
- An object of this invention is tetrahydro naphthyl chemical compounds. vide a method for preparing such compounds.
- Example I The following ingredients were placed in a one liter flask and refluxed for 16 hours.
- Ar. tetrahydro-alpha-naphthylamine may be employed in the place of the ar. tetrahydro-betanaphthylamine to produce the corresponding thiourea.
- other acids which form water soluble salts with ar. tetrahydro-naphthylamines such as the hydrobromic, hydrofluoric, sulphuric, etc. may be employed in place of the hydrochloric.
- Other alkali thiocyanates such as the sodium and potassium thiocyanates may be employed in place of the ammonium thiocyanate.
- other inert solvents or reaction media such as dilute alcohol, dilute acetone and the like may be employed in place of the water.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
UNITED STATES PATENT OFFICE 2,055,608 AR. TETRAHYDRO-NAPHTHYL THIOUREAS Herbert A. Labs and Arthur L. Fox, Wilmington,
Del., assignors to E.
Delaware No Drawing. Application November 3, 1934, Serial No. 751,283
3 Claims. (Cl. 260-125) This invention relates to ar. tetrahydronaphthyl thioureas and methods the same.
An object of this invention is tetrahydro naphthyl chemical compounds. vide a method for preparing such compounds.
for preparing to provide ar.
thioureas which are new A further object is to pronew chemical Still other objects are to advance the art. Other objects will appear hereinafter.
These objects may be accomplished in accordance with the present invention which comprises reacting water soluble salts of acids and ar. tetrahydro-naphthylamines with alkali thiocyanates. The resulting products are ar. tetrahydro-naphthyl thioureas which pounds.
are new chemical com- These new chemical compounds are valuable intermediates for the preparation of safety paper chemicals and dyestuffs.
In order to more clearly illustrate our invention and the preferred mode of carrying the same into effect, the following example is given:
Example I The following ingredients were placed in a one liter flask and refluxed for 16 hours.
parts ar. tetrahydro beta naphthylamine, 300
parts water,
44: parts concentrated hydrochloric thalene. The amount of hydroch ployed is just enough to bring the loric acid emsolution to the edge of congo acidity. The solution remained clear for about one hour and then as the thiourea began to became turbid form. After 16 hours,
the flask was cooled rapidly with stirring and fied in the form of small shot-like yield was 100 parts of crude materi the ar. tetrahydro-beta-naphthyl thiourea solidicrystals. The al. The crude Pont de Nemours & Del., a corporation of material was recrystallized from 16 parts of alcohol giving a finely crystalline product melting at 174.6 to 1'75.8 C.
Analysis Theory N 13.21% N=13.5 8% S 15.27% S==15.52%
Ar. tetrahydro-alpha-naphthylamine may be employed in the place of the ar. tetrahydro-betanaphthylamine to produce the corresponding thiourea. Also, other acids which form water soluble salts with ar. tetrahydro-naphthylamines such as the hydrobromic, hydrofluoric, sulphuric, etc. may be employed in place of the hydrochloric. Other alkali thiocyanates such as the sodium and potassium thiocyanates may be employed in place of the ammonium thiocyanate. Also, other inert solvents or reaction media such as dilute alcohol, dilute acetone and the like may be employed in place of the water.
While we have disclosed the preferred form of our invention and the preferred mode of carrying the same into efiect, it will be readily apparent to those skilled in the art that variations and modifications may be made therein, particularly in the relative proportions thereof without departing from the spirit of our invention. Accordingly, the scope of our invention is to be limited solely by the appended claims construed as broadly as is permissible in view of the prior art.
We claim:
1. An unsubstituted ar. thiourea.
2. Ar. tetrahydro beta-naphthyl thiourea.
3. Ar. tetrahydro alpha-naphthyl thiourea.
HERBERT A. LUBS. ARTHUR L. FOX.
tetrahydro naphthyl
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US751283A US2055608A (en) | 1934-11-03 | 1934-11-03 | Ar. tetrahydro-naphthyl thioureas |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US751283A US2055608A (en) | 1934-11-03 | 1934-11-03 | Ar. tetrahydro-naphthyl thioureas |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2055608A true US2055608A (en) | 1936-09-29 |
Family
ID=25021315
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US751283A Expired - Lifetime US2055608A (en) | 1934-11-03 | 1934-11-03 | Ar. tetrahydro-naphthyl thioureas |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2055608A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450406A (en) * | 1945-11-05 | 1948-10-05 | Parke Davis & Co | Process for obtaining thiosemicarbazide |
| US4868210A (en) * | 1988-03-30 | 1989-09-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic compounds and compositions |
-
1934
- 1934-11-03 US US751283A patent/US2055608A/en not_active Expired - Lifetime
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2450406A (en) * | 1945-11-05 | 1948-10-05 | Parke Davis & Co | Process for obtaining thiosemicarbazide |
| US4868210A (en) * | 1988-03-30 | 1989-09-19 | Warner-Lambert Company | Antihyperlipidemic and antiatherosclerotic compounds and compositions |
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