IE44369L - Triazine preparation - Google Patents

Triazine preparation

Info

Publication number
IE44369L
IE44369L IE96276A IE96276A IE44369L IE 44369 L IE44369 L IE 44369L IE 96276 A IE96276 A IE 96276A IE 96276 A IE96276 A IE 96276A IE 44369 L IE44369 L IE 44369L
Authority
IE
Ireland
Prior art keywords
give
cpd
treating
alkyl
formula
Prior art date
Application number
IE96276A
Other versions
IE44369B1 (en
Original Assignee
Du Pont
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 Du Pont filed Critical Du Pont
Publication of IE44369L publication Critical patent/IE44369L/en
Publication of IE44369B1 publication Critical patent/IE44369B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
    • C07D251/40—Nitrogen atoms
    • C07D251/42—One nitrogen atom
    • C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Prepn. of triazine herbicides of formula (I): (where R' is 2-8C alkyl, 5-8C cycloalkyl, norbornyl, methylcyclohexyl, methylcyclopentyl, phenyl or chlorophenyl; R3 is Me; R4 is 1-4C alkyl) is by (a) treatingcyanamide with an alkyl chloroformate RO2C.Cl to give an alkoxycarbonylcyanamide; (b) treating the prod. with an alkylating agent CH3.Z to give an N-Alkoxy-carbonyl-N-methylcyanamide; (c) treating this cpd. with an amine salt of formula R3R4.NH2 +n.Yn-5 (where n is 1 when Y is Cl-; n is 2 when Y is SO4--) to give a cpd. of formula RO2CN(CH3)C(=NH2)NR3R4 + Yn-; (d) treating this cpd. with an alkali metal hydroxide to give a cpd. of formula: RO2CN(CH3)C(=NH)NR3R4; (e) removing unreacted amine R3R4NH; (f) treating the prod. from (d) with an isocyanate R1.NCO to give a cpd. RO2CN(CH3)C(=NCONHR') NR3R4; (g) treating the prod. with a base M1.OR5 to cyclise it and give (I). (where Z is Br, I or -O3S.OMe; M' is an alkali metal; R is 2-3 C alkyl, R5 is 1-4C alkyl). Process gives increased yields compared with the 5-s stage process of US 3850924, esp. when R is Et. In an example, 1a-methyl-4-cyclohexyl-6-dimethylamino-s-triazine-2, 4(1H,3H)dione was prepd. [FR2310349A1]
IE96276A 1975-05-05 1976-05-05 Improvement in process for preparing herbicidal triazines and herbicidal triazine intermediates IE44369B1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US57435175A 1975-05-05 1975-05-05
US67592176A 1976-04-15 1976-04-15

Publications (2)

Publication Number Publication Date
IE44369L true IE44369L (en) 1976-11-05
IE44369B1 IE44369B1 (en) 1981-11-04

Family

ID=27076366

Family Applications (1)

Application Number Title Priority Date Filing Date
IE96276A IE44369B1 (en) 1975-05-05 1976-05-05 Improvement in process for preparing herbicidal triazines and herbicidal triazine intermediates

Country Status (8)

Country Link
AU (1) AU509813B2 (en)
BR (1) BR7602779A (en)
ES (1) ES447625A1 (en)
FR (2) FR2310349A1 (en)
IE (1) IE44369B1 (en)
MX (1) MX3778E (en)
PH (1) PH14092A (en)
PT (1) PT65067B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106380425A (en) * 2016-08-25 2017-02-08 宿迁市万和泰化工有限公司 Production process of N-(N-cyclohexylamide-N', N'-dmethyl amidine)-N-methyl ethyl carbamate
CN111763158B (en) * 2020-06-24 2022-09-09 江苏蓝丰生物化工股份有限公司 Preparation method of hexazinone intermediate guanidine compound and method for preparing hexazinone

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL42103A (en) * 1972-05-24 1976-05-31 Du Pont 6-amino-s-triazine-2,4-(1h,3h)-diones and corresponding 4-thio compounds,their preparation and their use as herbicides

Also Published As

Publication number Publication date
IE44369B1 (en) 1981-11-04
FR2349572B1 (en) 1981-01-02
ES447625A1 (en) 1977-10-01
FR2349572A1 (en) 1977-11-25
AU509813B2 (en) 1980-05-29
PT65067B (en) 1978-06-03
MX3778E (en) 1981-07-07
FR2310349A1 (en) 1976-12-03
PT65067A (en) 1976-06-01
BR7602779A (en) 1976-11-09
PH14092A (en) 1981-02-10
FR2310349B1 (en) 1980-11-07
AU1362876A (en) 1977-11-10

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