CA1069134A - 2-chloromethylphenylcarbamic acid fluoride - Google Patents
2-chloromethylphenylcarbamic acid fluorideInfo
- Publication number
- CA1069134A CA1069134A CA245,419A CA245419A CA1069134A CA 1069134 A CA1069134 A CA 1069134A CA 245419 A CA245419 A CA 245419A CA 1069134 A CA1069134 A CA 1069134A
- Authority
- CA
- Canada
- Prior art keywords
- acid
- acid fluoride
- hydrofluoric acid
- chloromethylphenylcarbamic
- fluoride
- 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
- QRPINPSYMPXPBD-UHFFFAOYSA-N n-[2-(chloromethyl)phenyl]carbamoyl fluoride Chemical compound FC(=O)NC1=CC=CC=C1CCl QRPINPSYMPXPBD-UHFFFAOYSA-N 0.000 title claims abstract description 11
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 39
- XTYOTPBIDRGAML-UHFFFAOYSA-N 1-(chloromethyl)-2-isocyanatobenzene Chemical compound ClCC1=CC=CC=C1N=C=O XTYOTPBIDRGAML-UHFFFAOYSA-N 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
- 229960002050 hydrofluoric acid Drugs 0.000 description 16
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- PVXRCPDNJSFYBV-UHFFFAOYSA-N carbamoyl fluoride Chemical compound NC(F)=O PVXRCPDNJSFYBV-UHFFFAOYSA-N 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 229940091249 fluoride supplement Drugs 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- QKKFUOJEGJTLIE-UHFFFAOYSA-N CC1(C=CC=CC1N=C=O)Cl Chemical compound CC1(C=CC=CC1N=C=O)Cl QKKFUOJEGJTLIE-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- DHFIERDILVVLTA-UHFFFAOYSA-N N-(2-chlorophenyl)-N-methylcarbamoyl fluoride Chemical compound ClC1=C(C=CC=C1)N(C(=O)F)C DHFIERDILVVLTA-UHFFFAOYSA-N 0.000 description 1
- 208000036366 Sensation of pressure Diseases 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 230000002921 anti-spasmodic effect Effects 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000005660 chlorination reaction Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000002222 fluorine compounds Chemical class 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 150000003951 lactams Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910000000 metal hydroxide Inorganic materials 0.000 description 1
- 150000004692 metal hydroxides Chemical class 0.000 description 1
- DZXAINSCQJRLEG-UHFFFAOYSA-N n-phenylcarbamoyl fluoride Chemical compound FC(=O)NC1=CC=CC=C1 DZXAINSCQJRLEG-UHFFFAOYSA-N 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/20—Dibenz [b, e] azepines; Hydrogenated dibenz [b, e] azepines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752505714 DE2505714C3 (de) | 1975-02-12 | 2-Chlormethylphenylcarbamidsaurefluorid Verfahren zu seiner Herstellung sowie seine Verwendung zur Herstellung von 2-Aminodiphenylmethan-2'-carbonsäurelaetam |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1069134A true CA1069134A (en) | 1980-01-01 |
Family
ID=5938612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA245,419A Expired CA1069134A (en) | 1975-02-12 | 1976-02-10 | 2-chloromethylphenylcarbamic acid fluoride |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4058561A (show.php) |
| JP (1) | JPS564543B2 (show.php) |
| BE (1) | BE838416A (show.php) |
| CA (1) | CA1069134A (show.php) |
| CH (1) | CH619448A5 (show.php) |
| ES (1) | ES445072A1 (show.php) |
| FR (1) | FR2300758A1 (show.php) |
| GB (1) | GB1479573A (show.php) |
| IT (1) | IT1053832B (show.php) |
| NL (1) | NL7601290A (show.php) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH646946A5 (de) * | 1979-06-01 | 1984-12-28 | Upjohn Co | Verfahren zur herstellung von n-methylcarbamoyl-fluorid. |
| CN103130717B (zh) * | 2011-11-29 | 2015-04-01 | 上海博康精细化工有限公司 | 二苯并氮卓酮的制备方法 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2974163A (en) * | 1958-08-11 | 1961-03-07 | Du Pont | Production of para-chlorophenyl carbamyl chloride |
| US3041364A (en) * | 1959-12-18 | 1962-06-26 | Du Pont | Process of preparing 4, 4'-diisocyanatodiphenyl sulfides |
| US3262974A (en) * | 1962-01-31 | 1966-07-26 | Stamicarbon | Process for the preparation of carbamyl chloride |
| DE1294369B (de) * | 1966-05-11 | 1969-05-08 | Bayer Ag | Verfahren zur Herstellung von Trifluormethylisocyanat |
-
1976
- 1976-01-23 US US05/651,995 patent/US4058561A/en not_active Expired - Lifetime
- 1976-02-09 NL NL7601290A patent/NL7601290A/xx not_active Application Discontinuation
- 1976-02-09 CH CH154476A patent/CH619448A5/de not_active IP Right Cessation
- 1976-02-10 IT IT48028/76A patent/IT1053832B/it active
- 1976-02-10 BE BE164204A patent/BE838416A/xx unknown
- 1976-02-10 JP JP1291476A patent/JPS564543B2/ja not_active Expired
- 1976-02-10 CA CA245,419A patent/CA1069134A/en not_active Expired
- 1976-02-11 GB GB5392/76A patent/GB1479573A/en not_active Expired
- 1976-02-11 ES ES445072A patent/ES445072A1/es not_active Expired
- 1976-02-12 FR FR7603890A patent/FR2300758A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| FR2300758B1 (show.php) | 1982-01-22 |
| JPS564543B2 (show.php) | 1981-01-30 |
| ES445072A1 (es) | 1977-05-16 |
| JPS51105033A (show.php) | 1976-09-17 |
| DE2505714A1 (de) | 1976-08-26 |
| NL7601290A (nl) | 1976-08-16 |
| GB1479573A (en) | 1977-07-13 |
| CH619448A5 (show.php) | 1980-09-30 |
| IT1053832B (it) | 1981-10-10 |
| BE838416A (fr) | 1976-08-10 |
| DE2505714B2 (de) | 1977-03-03 |
| US4058561A (en) | 1977-11-15 |
| FR2300758A1 (fr) | 1976-09-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |