JPH03382B2 - - Google Patents
Info
- Publication number
- JPH03382B2 JPH03382B2 JP13184882A JP13184882A JPH03382B2 JP H03382 B2 JPH03382 B2 JP H03382B2 JP 13184882 A JP13184882 A JP 13184882A JP 13184882 A JP13184882 A JP 13184882A JP H03382 B2 JPH03382 B2 JP H03382B2
- Authority
- JP
- Japan
- Prior art keywords
- thiourea
- reaction
- formula
- trifluoromethylpropanal
- component
- 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
Links
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 23
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 11
- QLHMHPBDSYKXRI-UHFFFAOYSA-N 3,3,3-trifluoro-2-methylpropanal Chemical compound O=CC(C)C(F)(F)F QLHMHPBDSYKXRI-UHFFFAOYSA-N 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 6
- 150000003585 thioureas Chemical class 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 2
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 10
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 239000013078 crystal Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-WFGJKAKNSA-N acetone d6 Chemical compound [2H]C([2H])([2H])C(=O)C([2H])([2H])[2H] CSCPPACGZOOCGX-WFGJKAKNSA-N 0.000 description 3
- 238000000921 elemental analysis Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- -1 aliphatic aldehydes Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 238000006482 condensation reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 230000000704 physical effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- FDMFUZHCIRHGRG-UHFFFAOYSA-N 3,3,3-trifluoroprop-1-ene Chemical compound FC(F)(F)C=C FDMFUZHCIRHGRG-UHFFFAOYSA-N 0.000 description 1
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Description
本発明はチオ尿素誘導体に関する。さらに詳し
くは、チオ尿素とトリフルオロメチルプロパナー
ルの縮合体に関する。
チオ尿素と種々の脂肪族アルデヒドの縮合体お
よびその製造法に関しては従来より数多く知られ
ているが、トリフルオロメチルプロパナールとの
縮合体は知られていない。
本発明者は、脂肪族アルデヒドではあるが、ふ
つ素をその構造中に有するトリフルオロメチルプ
ロパナールに注目し、チオ尿素との反応を試みた
結果、興味深い縮合体を得ることができ、本発明
に到達した。
即ち、本発明はチオ尿素とトリフルオロメチル
プロパナールの縮合体に関するものであり、それ
は次の一般式(1)で表わす反応で得ることができ
る。
H2N−CS−NH2＋CH3CH（CF3）CHO→R1−
NH−CS−NH−R2 (1)
（）
ここに縮合体（）においてR1−はCH3C
（CF3）＝CH−またはCH3CH（CF3）−CH（NH−
CS−NH2）−を示し、またR2−はＨ−、CH3C
（CF3）＝CH−またはCH3CH（CF3）−CH（NH−
CS−NH2）−を示す。
本発明における縮合反応(1)は通常、溶媒中で行
うのが好適であり溶媒としてはトルエン、ジオキ
サン、テトラヒドロフラン、エーテル、DMF、
ベンゼン、アセトニトリル、クロロホルム、１，
２−ジクロルエタン、酢酸エチル、アセトン等が
適当である。
本発明における反応(1)の温度は室温ないし、用
いる溶媒の沸点までの範囲内で可能である。
本発明の反応(1)において用いるチオ尿素とトリ
フルオロメチルプロパナールの割合はモル比で３
対１ないし１対３が適当である。
本発明の反応(1)においては特に触媒を必要とせ
ず、室温ないし溶媒の沸点において数時間ないし
数10時間攪拌するだけで反応を進行させることが
できる。但し縮合反応であるため脱水剤を用いる
と反応を生成物側に有利に導くことができる。脱
水剤としては硫酸ナトリウム、硫酸マグネシウム
またはモレキユラーシーブス等が適している。
本発明の原料の１つであるトリフルオロメチル
プロパナールは例えば３，３，３−トリフルオロ
プロペンをオキソ反応に附することにより高収率
で得られる化合物である。
本発明において得られるふつ素を含んだチオ尿
素誘導体は文献未載の新規物質であつて、抗菌作
用を示し、医薬、濃薬の中間原料として有用な物
質である。
実施例 １
チオ尿素7.6ｇ（0.1mol）をジオキサン20mlに
分散し、トリフルオロメチルプロパナール12.6ｇ
（0.1mol）を加えて10時間還流した。反応後、溶
媒を留去し酢酸エチル20mlを加えて不溶分を除い
た後、シリカゲル−クロロホルム−酢酸エチル系
にてカラムクロマトグラフイーを行い、主な成分
A0.8ｇ、B5.5ｇ、C3.6ｇの３種を得た。
成分Ａはトルエンより再結晶することにより無
色の結晶となり、Ｎ，N′−ビス〔（２−トリフル
オロメチル）−プロペニル〕チオ尿素（）であ
つた。
〔CH3（CF3）＝CH−NH〕−2C＝Ｓ （）
Mp：166−７〔℃〕（dec）；
IRmax（KBrdisk）：3450，3290，3225，3130，
3070，1694，1540，1380，1340，1300，1255，
1160，1105，1080，987，900，888，798，760，
715，690，600〔cm-1〕1
H−NMR（Acetone−d6、TMS）：δ1.83（Ｓ，
6H，ＣＨ 3）、7.92（ｄ，2H，Ｊ＝10 Hz，＝ＣＨ
−）、9.23（ｄ，2H，Ｊ＝10Hz，−ＮＨ−）〔ppm〕
元素分析：Ｃ 37.18、Ｈ 3.31、Ｎ 9.73〔％〕
同計算値（C9F6H10N2Sとして）：Ｃ 36.99，Ｈ
3.45，Ｎ 9.59〔％〕
Mass：ｍ／ｅ、292（m+）、293（m+＋１）；計算
値292（ｍ）
一方成分Ｂはトルエンより再結晶することによ
り無色の針状晶となり、Ｎ−（２−トリフルオロ
メチル）−プロペニルチオ尿素（）であつた。
CH3C（CF3）＝CH−NH−CS−NH2 （）
Mp：140−１℃（dec.）
IRmax（KBr disk）：3520，3385，3220，3190，
3100，1698，1612，1555，1360，1340，1297，
1240，1152，1110，910，800，750，696，667，
600〔cm-1〕1
H−NMR（Acetone−d6，TMS）：δ 1.82（Ｓ，
3H，ＣＨ 3）、7.90（ｄ，1H，Ｊ＝10Hz，＝ＣＨ−
NH−）、7.38（bs，2H，−ＮＨ 2）、8.98（ｄ，1H，
Ｊ＝10Hz，CH−ＮＨ−）〔ppm〕
元素分析：Ｃ 32.98、Ｈ 3.69、Ｎ 15.36〔％〕
同計算値〔C5F3H7N2Sとして〕：Ｃ 32.61、Ｈ
3.83、Ｎ 15，21〔％〕
Mass：ｍ／ｅ、184（m+）；計算値184（ｍ）
また、成分Ｃはエーテルに溶解し、ヘキサンで
結晶化させることにより黄色の結晶となりＮ，
N′−ビス〔（１−チオウレイド−２−トリフルオ
ロメチル）−プロピル〕チオ尿素（）であつた。
Mp：120−40〔℃〕（dec）
IRmax（KBrdisk）：3300，3200，1610，1515，
1415，1350，1260，1180，1150，1120，795，745
〔cm-1〕1
H−NMR（Acetone−d6、TMS）：1.27（ｄ，
6H，Ｊ＝７Hz，ＣＨ 3）、2.9−3.7（broad ｍ，
2H，
The present invention relates to thiourea derivatives. More specifically, it relates to a condensate of thiourea and trifluoromethylpropanal. Although many condensates of thiourea and various aliphatic aldehydes and their production methods have been known, condensates of trifluoromethylpropanal have not been known. The present inventor focused on trifluoromethylpropanal, which is an aliphatic aldehyde but has fluorine in its structure, and attempted to react with thiourea, and as a result, was able to obtain an interesting condensate. reached. That is, the present invention relates to a condensate of thiourea and trifluoromethylpropanal, which can be obtained by the reaction represented by the following general formula (1). H 2 N−CS−NH 2 +CH 3 CH(CF 3 )CHO→R 1 −
NH−CS−NH−R 2 (1) () Here, in the condensate (), R 1 − is CH 3 C
(CF 3 )=CH− or CH 3 CH(CF 3 )−CH(NH−
CS-NH 2 )-, and R 2 - is H-, CH 3 C
(CF 3 )=CH− or CH 3 CH(CF 3 )−CH(NH−
CS−NH 2 )− is shown. The condensation reaction (1) in the present invention is usually preferably carried out in a solvent, and examples of the solvent include toluene, dioxane, tetrahydrofuran, ether, DMF,
Benzene, acetonitrile, chloroform, 1,
2-dichloroethane, ethyl acetate, acetone, etc. are suitable. The temperature of reaction (1) in the present invention can range from room temperature to the boiling point of the solvent used. The molar ratio of thiourea and trifluoromethylpropanal used in reaction (1) of the present invention is 3.
A ratio of 1:1 to 1:3 is appropriate. Reaction (1) of the present invention does not particularly require a catalyst, and the reaction can proceed simply by stirring for several hours to several tens of hours at room temperature to the boiling point of the solvent. However, since this is a condensation reaction, using a dehydrating agent can advantageously direct the reaction toward the product side. Suitable dehydrating agents include sodium sulfate, magnesium sulfate, and molecular sieves. Trifluoromethylpropanal, which is one of the raw materials of the present invention, is a compound obtained in high yield by subjecting 3,3,3-trifluoropropene to an oxo reaction. The fluorine-containing thiourea derivative obtained in the present invention is a new substance that has not been described in any literature, exhibits antibacterial activity, and is a useful substance as an intermediate raw material for pharmaceuticals and concentrated drugs. Example 1 7.6 g (0.1 mol) of thiourea was dispersed in 20 ml of dioxane, and 12.6 g of trifluoromethylpropanal was added.
(0.1 mol) was added and refluxed for 10 hours. After the reaction, the solvent was distilled off and 20 ml of ethyl acetate was added to remove insoluble matter, followed by column chromatography using a silica gel-chloroform-ethyl acetate system to separate the main components.
Three types were obtained: 0.8 g of A, 5.5 g of B, and 3.6 g of C. Component A became colorless crystals by recrystallization from toluene, and was N,N'-bis[(2-trifluoromethyl)-propenyl]thiourea (). [CH 3 (CF 3 )=CH−NH] − 2 C=S () Mp: 166−7 [℃] (dec); IRmax (KBrdisk): 3450, 3290, 3225, 3130,
3070, 1694, 1540, 1380, 1340, 1300, 1255,
1160, 1105, 1080, 987, 900, 888, 798, 760,
715, 690, 600 [cm -1 ] 1 H-NMR (Acetone-d 6 , TMS): δ1.83 (S,
6H, C H 3 ), 7.92 (d, 2H, J = 10 Hz, = C H
-), 9.23 (d, 2H, J = 10Hz, -N H -) [ppm] Elemental analysis: C 37.18, H 3.31, N 9.73 [%] Same calculated value (as C 9 F 6 H 10 N 2 S) :C 36.99,H
3.45, N 9.59 [%] Mass: m/e, 292 (m + ), 293 (m + +1); calculated value 292 (m) On the other hand, component B becomes colorless needle-like crystals by recrystallizing from toluene. It was N-(2-trifluoromethyl)-propenylthiourea (). CH 3 C (CF 3 ) = CH-NH-CS-NH 2 () Mp: 140-1℃ (dec.) IRmax (KBr disk): 3520, 3385, 3220, 3190,
3100, 1698, 1612, 1555, 1360, 1340, 1297,
1240, 1152, 1110, 910, 800, 750, 696, 667,
600 [cm -1 ] 1 H-NMR (Acetone-d 6 , TMS): δ 1.82 (S,
3H, CH 3 ), 7.90 (d, 1H, J = 10Hz, = CH -
NH-), 7.38 (bs, 2H, -NH 2 ), 8.98 (d, 1H,
J=10Hz, CH- NH- ) [ppm] Elemental analysis: C 32.98, H 3.69, N 15.36 [%] Same calculated value [as C 5 F 3 H 7 N 2 S]: C 32.61, H
3.83, N 15,21 [%] Mass: m/e, 184 (m + ); calculated value 184 (m) In addition, component C becomes yellow crystals by dissolving in ether and crystallizing with hexane, N,
It was N'-bis[(1-thiourido-2-trifluoromethyl)-propyl]thiourea (). Mp: 120−40 [℃] (dec) IRmax (KBrdisk): 3300, 3200, 1610, 1515,
1415, 1350, 1260, 1180, 1150, 1120, 795, 745
[cm -1 ] 1 H-NMR (Acetone-d 6 , TMS): 1.27 (d,
6H, J=7Hz, CH3 ), 2.9−3.7 (broad m,
2H,
【式】）、6.32（bq，2H，Ｊ＝ ８Hz，[Formula]), 6.32 (bq, 2H, J= 8Hz,
【式】）、7.28（broad Ｓ，
4H−NH2）、7.28（bd，4H，Ｊ＝８Hz，
[Formula]), 7.28 (broad S, 4H−NH 2 ), 7.28 (bd, 4H, J=8Hz,
【式】）〔ppm〕
元素分析：Ｃ 30.96、Ｈ 4.58、Ｎ 19.00〔％〕
同計算値（C11F6H18N6S3として）：Ｃ 29.73、
Ｈ 4.08、Ｎ 18.91〔％〕
Nass：ｍ／ｅ、fragment 308（m+−tiourea−
[Formula]) [ppm] Elemental analysis: C 30.96, H 4.58, N 19.00 [%] Same calculated value (as C 11 F 6 H 18 N 6 S 3 ): C 29.73,
H 4.08, N 18.91 [%] Nass: m/e, fragment 308 (m + −tiourea−
【式】）、292（m+−2tiourea）、223（292−
CH3）；計算値444（ｍ）
実施例 ２
チオ尿素3.8ｇ（0.05mol）をジオキサン50mlに
溶解しトリフルオロメチルプロパナール12.6ｇ
（0.1mol）を加えて室温に40時間攪拌し、次いで
硫酸マグネシウム12ｇを加えて20時間還流させ
た。反応溶液のTLCによる分析では成分Ａおよ
び成分Ｂが主に生成していることが確かめられ
た。反応後不溶解分をろ別し、減圧下に濃縮後、
クロロホルム５mlから再結晶し成分Ｂ主体の部分
1.5ｇを得た。
ろ液を濃縮し、得られた褐色粘稠液7.6ｇをシ
リカゲル−クロロホルム−酢酸エチル系でクロマ
トグラフイーを行い成分A1.7ｇおよび成分B1.1
ｇに分けた。成分Ｂは上述のクロロホルムよりの
再結晶物と合わせトルエンより再結晶することに
よりほゞ無色の結晶として得られ、諸物性の測定
によりチオ尿素縮合体（）と全く同一物である
ことを確認した。
また成分Ａはトルエンより再結晶することによ
り、ほゞ無色の結晶となり諸物性の測定によりチ
オ尿素縮合体（）と全く同一物質であることを
確認した。[Formula]), 292 (m + -2tiourea), 223 (292- CH 3 ); Calculated value 444 (m) Example 2 Thiourea 3.8g (0.05mol) was dissolved in dioxane 50ml and trifluoromethylpropanal 12.6 g
(0.1 mol) and stirred at room temperature for 40 hours, then 12 g of magnesium sulfate was added and refluxed for 20 hours. Analysis of the reaction solution by TLC confirmed that component A and component B were mainly produced. After the reaction, undissolved matter was filtered out and concentrated under reduced pressure.
Recrystallized from 5 ml of chloroform and mainly contains component B.
1.5g was obtained. The filtrate was concentrated, and 7.6 g of the resulting brown viscous liquid was chromatographed using a silica gel-chloroform-ethyl acetate system to obtain 1.7 g of component A and 1.1 g of component B.
Divided into g. Component B was obtained as almost colorless crystals by combining with the above-mentioned recrystallized product from chloroform and recrystallizing from toluene, and it was confirmed by measurement of various physical properties that it was exactly the same as the thiourea condensate (). . Component A was recrystallized from toluene to form almost colorless crystals, and measurements of various physical properties confirmed that it was exactly the same substance as the thiourea condensate ().
Claims (1)
て、R1−はCH3C（CF3）＝CH−またはCH3CH
（CF3）−CH（NH−CS−NH2）−を表し、R2−は
Ｈ−、CH3C（CF3）＝CH−またはCH3CH（CF3）
−CH（NH−CS−NH2）−を表わす。 ２ 化学式〔CH3C（CF3）＝CH−NH〕−2C＝Ｓで
表わされる第１項記載のチオ尿素誘導体。 ３ 化学式CH3C（CF3）＝CH−NH−CS−NH2
で表わされる第１項記載のチオ尿素誘導体。 ４ 化学式〔CH3CH（CF3）−CH（NH−CS−
NH2）−NH〕−2C＝Ｓで表わされる第１項記載の
チオ尿素誘導体。 ５ チオ尿素とトリフルオロメチルプロパナール
とを反応させることを特徴とする一般式 R1−
NH−CS−NH−R2（ここに、R1−はCH3C（CF3）
＝CH−またはCH3CH（CF3）−CH（NH−CS−
CH2）−を表わし、R2−はＨ−、CH3C（CF3）＝
CH−またはCH3CH（CF3）−CH（NH−CS−
NH2）−を表わす。）で表わされる化合物の製法。[Claims] 1. A thiourea derivative represented by the general formula [Formula]. However, in this formula, R 1 - is CH 3 C (CF 3 ) = CH- or CH 3 CH
( CF3 )-CH(NH-CS- NH2 )-, R2- is H-, CH3C ( CF3 )=CH- or CH3CH ( CF3 )
-CH(NH-CS- NH2 )-. 2. The thiourea derivative according to item 1, which is represented by the chemical formula [ CH3C ( CF3 )=CH-NH] -2C =S. 3 Chemical formula CH3C ( CF3 )=CH-NH-CS- NH2
The thiourea derivative according to item 1, which is represented by: 4 Chemical formula [CH 3 CH (CF 3 )-CH (NH-CS-
2. The thiourea derivative according to item 1, which is represented by NH2 )-NH] -2C =S. 5 General formula R 1 − characterized by reacting thiourea and trifluoromethylpropanal
NH−CS−NH−R 2 (here, R 1 − is CH 3 C (CF 3 )
=CH- or CH3CH ( CF3 )-CH(NH-CS-
CH 2 )−, R 2 − is H−, CH 3 C(CF 3 )=
CH− or CH 3 CH(CF 3 )−CH(NH−CS−
NH 2 )−. ) The method for producing the compound represented by
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13184882A JPS5921663A (en) | 1982-07-28 | 1982-07-28 | Fluorine-containing thiourea derivative and its preparation |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13184882A JPS5921663A (en) | 1982-07-28 | 1982-07-28 | Fluorine-containing thiourea derivative and its preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5921663A JPS5921663A (en) | 1984-02-03 |
| JPH03382B2 true JPH03382B2 (en) | 1991-01-07 |
Family
ID=15067520
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13184882A Granted JPS5921663A (en) | 1982-07-28 | 1982-07-28 | Fluorine-containing thiourea derivative and its preparation |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS5921663A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2647112A1 (en) * | 1989-05-22 | 1990-11-23 | Atochem | NITROGEN POLYFLUORALKYL COMPOUNDS, PROCESSES FOR THEIR PREPARATION AND THEIR APPLICATIONS |
-
1982
- 1982-07-28 JP JP13184882A patent/JPS5921663A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5921663A (en) | 1984-02-03 |
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