JPS6327339B2 - - Google Patents
Info
- Publication number
- JPS6327339B2 JPS6327339B2 JP54039838A JP3983879A JPS6327339B2 JP S6327339 B2 JPS6327339 B2 JP S6327339B2 JP 54039838 A JP54039838 A JP 54039838A JP 3983879 A JP3983879 A JP 3983879A JP S6327339 B2 JPS6327339 B2 JP S6327339B2
- Authority
- JP
- Japan
- Prior art keywords
- reaction
- dimethylamine
- tetramethyl guanidine
- solvent
- yield
- 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
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 40
- 238000006243 chemical reaction Methods 0.000 claims description 27
- KYVBNYUBXIEUFW-UHFFFAOYSA-N 1,1,3,3-tetramethylguanidine Chemical class CN(C)C(=N)N(C)C KYVBNYUBXIEUFW-UHFFFAOYSA-N 0.000 claims description 16
- -1 cyanogen halide Chemical class 0.000 claims description 10
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 10
- 239000002904 solvent Substances 0.000 claims description 7
- 239000003125 aqueous solvent Substances 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 6
- 239000007810 chemical reaction solvent Substances 0.000 claims description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 238000000034 method Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- LINDOXZENKYESA-UHFFFAOYSA-N TMG Natural products CNC(N)=NC LINDOXZENKYESA-UHFFFAOYSA-N 0.000 description 6
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 4
- QPJDMGCKMHUXFD-UHFFFAOYSA-N cyanogen chloride Chemical compound ClC#N QPJDMGCKMHUXFD-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- GESRUPNWDGSYQI-UHFFFAOYSA-N bromylformonitrile Chemical compound O=Br(=O)C#N GESRUPNWDGSYQI-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002994 raw material Substances 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 2
- IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 2
- OAGOUCJGXNLJNL-UHFFFAOYSA-N dimethylcyanamide Chemical compound CN(C)C#N OAGOUCJGXNLJNL-UHFFFAOYSA-N 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010037660 Pyrexia Diseases 0.000 description 1
- SKIUIUTXTJCPQE-UHFFFAOYSA-N [amino(dimethylamino)methylidene]-dimethylazanium;bromide Chemical compound [Br-].CN(C)C(=N)[NH+](C)C SKIUIUTXTJCPQE-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000000779 smoke Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3983879A JPS55133352A (en) | 1979-04-04 | 1979-04-04 | Preparation of 1,1,3,3-tetramethyl guanidine salt |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP3983879A JPS55133352A (en) | 1979-04-04 | 1979-04-04 | Preparation of 1,1,3,3-tetramethyl guanidine salt |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS55133352A JPS55133352A (en) | 1980-10-17 |
| JPS6327339B2 true JPS6327339B2 (xx) | 1988-06-02 |
Family
ID=12564095
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP3983879A Granted JPS55133352A (en) | 1979-04-04 | 1979-04-04 | Preparation of 1,1,3,3-tetramethyl guanidine salt |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS55133352A (xx) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4573006B2 (ja) * | 1999-07-29 | 2010-11-04 | 三菱瓦斯化学株式会社 | ジメチルシアナミド及び１，１，３，３−テトラメチルグアニジンの製造方法 |
| DE60005613T2 (de) | 1999-07-29 | 2004-08-12 | Mitsubishi Gas Chemical Co., Inc. | Verfahren zur Herstellung von Dimethylcyanamid |
| CN1304368C (zh) * | 2004-10-12 | 2007-03-14 | 山东新华万博化工有限公司 | 生产四甲基胍的改进工艺 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4948932A (xx) * | 1972-09-13 | 1974-05-11 |
-
1979
- 1979-04-04 JP JP3983879A patent/JPS55133352A/ja active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4948932A (xx) * | 1972-09-13 | 1974-05-11 |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55133352A (en) | 1980-10-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6613908B2 (en) | Method for carbamoylating alcohols | |
| HU203326B (en) | Process for producing 1,2-bis(3,5-dioxo-piperazin-1-yl)-propane | |
| JPS6327339B2 (xx) | ||
| JPS6023351A (ja) | ２−アミノ−３，５−ジブロムベンジルアミン類の製法 | |
| Lee et al. | The Novel Synthesis of Two Diastereomers of γ-Hydroxyproline | |
| JPS6054311B2 (ja) | ２−イソプロピルアミノピリミジンの製造法 | |
| JPH0558985A (ja) | シアノグアニジン誘導体の製造法 | |
| JPS6160673A (ja) | グアニジノチアゾ−ル誘導体の製造法 | |
| JP3042123B2 (ja) | Ｎ−シアノアセトアミジン誘導体の製法 | |
| JPS5849547B2 (ja) | ピラゾリンユウドウタイノ セイゾウホウ | |
| JPH0219348A (ja) | セレジリン塩酸塩の製造方法 | |
| SU1082318A3 (ru) | Способ выделени / @ /-1,2-дифенил-1-/ @ -/2-диметиламиноэтокси /-фенил/-бутена-1 или его солей | |
| US4189444A (en) | Process for the preparation of N,N'-disubstituted 2-naphthaleneethanimidamide and intermediates used therein | |
| US2994696A (en) | Process for the preparation of vitamin-b1 halides | |
| KR100277510B1 (ko) | 테트라하이드로카르바졸론 유도체의 제조방법 | |
| JPS6343382B2 (xx) | ||
| JPS638104B2 (xx) | ||
| Bulgozdy et al. | The Preparation of Anhydrous Hydrazine and Deutero-hydrazine from Hydrazine Dihydrochloride1 | |
| JPS596865B2 (ja) | ５−（（２− ハロゲノ −１− ヒドロキシ ） アルキル ） カルボスチリルユウドウタイノセイゾウホウ | |
| JPS5936633B2 (ja) | ベンゾクマリン誘導体の製造法 | |
| JPH01313471A (ja) | Ｎ−スルフアモイルアミジン化合物の製造法 | |
| JPH06345735A (ja) | Ｎ−置換−３−ピペリジノールの製法 | |
| JPS607988B2 (ja) | ３―アミノ―５―第三ブチルイソオキサゾールの改良合成法 | |
| JPS603062B2 (ja) | ８−ヒドロキシカルボスチリル誘導体の製造法 | |
| JPS60115567A (ja) | ３−アミノイソオキサゾ−ル類の製法 |