GB1467687A - Monoester monochlorides of 2-chloromalonic acid - Google Patents

Monoester monochlorides of 2-chloromalonic acid

Info

Publication number
GB1467687A
GB1467687A GB5086974A GB5086974A GB1467687A GB 1467687 A GB1467687 A GB 1467687A GB 5086974 A GB5086974 A GB 5086974A GB 5086974 A GB5086974 A GB 5086974A GB 1467687 A GB1467687 A GB 1467687A
Authority
GB
United Kingdom
Prior art keywords
prepared
chloro
methyl
monochlorides
monoester
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
Application number
GB5086974A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
UCB SA
Original Assignee
UCB SA
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by UCB SA filed Critical UCB SA
Priority to GB5086974A priority Critical patent/GB1467687A/en
Priority to NL7513580A priority patent/NL7513580A/en
Priority to DE19752552629 priority patent/DE2552629A1/en
Priority to FR7535897A priority patent/FR2291966A1/en
Priority to BE1007020A priority patent/BE835852A/en
Publication of GB1467687A publication Critical patent/GB1467687A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D499/04—Preparation
    • C07D499/06—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
    • C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/08—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D277/12—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Biotechnology (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1467687 Monoester monochlorides of chloromalonic acids UCB 25 Nov 1975 [25 Nov 1974] 50869/74 Heading C2C Novel monoester monochlorides of 2-chloromalonic acid of the general formula wherein R is benzyl or C 1-5 straight or branched alkyl, are prepared by reacting a compound of general formula where Z is H or an alkali metal, with (COCl) 2 when Z is alkali metal and with an α-chlorenamine of formula in which X, X<SP>1</SP>, Y and Y<SP>1</SP>, same or different, are each alkyl, aryl, alkaryl or aralkyl or Y and Y<SP>1</SP> together with the N atom to which they are attached form a heterocyclic radical which is optionally substituted, when Z is H. Alternatively those esters other than where R = t-butyl are obtained by reacting N 2 = CH-COOR with COCl 2 in organic solution to give the corresponding product and then treating with HCl. In the examples the methyl, ethyl, t-butyl and benzyl derivatives are prepared. 3 - Chloro - 2 - oxo - 1,4 - diphenyl - azetidine- 3-carboxylate (I) is obtained from ethyl 2-chloromalonate acid chloride and benzaniline. The 1,4,4-diphenyl derivative is similarly prepared using N-(diphenylmethylene) aniline instead of benzaniline. 6 - Chloro - 3,3 - dimethyl - 7 - oxo - 4 - thia - 1- azabicyclo[3,2,0]heptane- 2,6 - dicarboxylate (II) is prepared from methyl 2-chloromalonate acid chloride and 5,5-dimethyl-4-methoxycarbonyl- #<SP>2</SP>-thiazoline. 7 - Chloro - 7 - methoxycarbonyl - [3,2,0] bicyclohepten-6-one (III) is obtained from methyl- 2-chloromalonate acid chloride and cyclopentadiene. Methyl - 5 - methoxycarbonyl - α - chloro - 2- cyclopentene - 1 - acetate is prepared by treating product (III) above with methanol.
GB5086974A 1974-11-25 1974-11-25 Monoester monochlorides of 2-chloromalonic acid Expired GB1467687A (en)

Priority Applications (5)

Application Number Priority Date Filing Date Title
GB5086974A GB1467687A (en) 1974-11-25 1974-11-25 Monoester monochlorides of 2-chloromalonic acid
NL7513580A NL7513580A (en) 1974-11-25 1975-11-20 PROCESS FOR PREPARING MONOESTERS-MONOCHLORIDES FROM 2-CHLORORMALONIC ACID.
DE19752552629 DE2552629A1 (en) 1974-11-25 1975-11-24 MONOESTER MONOCHLORIDE OF 2-CHLORMALONIC ACID, METHOD FOR THEIR PREPARATION AND USE
FR7535897A FR2291966A1 (en) 1974-11-25 1975-11-24 MONOESTERS-MONOCHLORIDES OF 2-CHLORO-MALONIC ACID FOR THE PREPARATION OF PENICILLIN AND PROSTAGLANDIN PRECURSORS
BE1007020A BE835852A (en) 1974-11-25 1975-11-24 MONDESTERS-MONOCHLORIDES OF 2-CHLORO-MALONIC ACID

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB5086974A GB1467687A (en) 1974-11-25 1974-11-25 Monoester monochlorides of 2-chloromalonic acid

Publications (1)

Publication Number Publication Date
GB1467687A true GB1467687A (en) 1977-03-16

Family

ID=10457712

Family Applications (1)

Application Number Title Priority Date Filing Date
GB5086974A Expired GB1467687A (en) 1974-11-25 1974-11-25 Monoester monochlorides of 2-chloromalonic acid

Country Status (5)

Country Link
BE (1) BE835852A (en)
DE (1) DE2552629A1 (en)
FR (1) FR2291966A1 (en)
GB (1) GB1467687A (en)
NL (1) NL7513580A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776351A (en) * 2017-11-15 2019-05-21 江苏优士化学有限公司 A kind of diazonium acetate is continuously synthesizing to method

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109776351A (en) * 2017-11-15 2019-05-21 江苏优士化学有限公司 A kind of diazonium acetate is continuously synthesizing to method
CN109776351B (en) * 2017-11-15 2021-11-09 江苏优士化学有限公司 Diazoacetic ester continuous synthesis method

Also Published As

Publication number Publication date
DE2552629A1 (en) 1976-05-26
FR2291966A1 (en) 1976-06-18
NL7513580A (en) 1976-05-28
BE835852A (en) 1976-05-24
FR2291966B1 (en) 1978-05-12

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Legal Events

Date Code Title Description
PS Patent sealed
PCNP Patent ceased through non-payment of renewal fee