GB776069A - Manufacture of substituted ureas - Google Patents

Manufacture of substituted ureas

Info

Publication number
GB776069A
GB776069A GB1550554A GB1550554A GB776069A GB 776069 A GB776069 A GB 776069A GB 1550554 A GB1550554 A GB 1550554A GB 1550554 A GB1550554 A GB 1550554A GB 776069 A GB776069 A GB 776069A
Authority
GB
United Kingdom
Prior art keywords
phenol
urea
dimethylurea
dimethylamine
phenyl
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
GB1550554A
Inventor
Richard Lewis Jones
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB1550554A priority Critical patent/GB776069A/en
Publication of GB776069A publication Critical patent/GB776069A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1854—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety
    • C07C273/1863—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas by reactions not involving the formation of the N-C(O)-N- moiety from urea

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

Organic compounds of the formula Ar.NHCONR1R11, wherein Ar is an aromatic radical which may optionally be substituted, R1 is an alkyl radical and R11 is hydrogen or an alkyl radical, are prepared by heating the corresponding primary aromatic amine of the formula ArNH2, wherein Ar has the meaning stated above, with an equimolecular proportion of urea and an equimolecular proportion or conveniently an excess of an alcohol or a phenol having a boiling-point between 100 DEG and 200 DEG C., and when the evolution of ammonia has ceased, passing into the hot molten product the corresponding mono- or dialkyl-amine until any excess of alcohol or phenol, if present, and also that which is formed during this stage of the reaction has been removed by distillation. Primary amines of the formula ArNH2 specified are aniline and halogenated anilines, e.g. p - chloro - and 3:4 - dichloroaniline. Suitable mono- and di-alkylamines of the formula HNR1R11 are mono- and di-methyl- and -ethyl-amines. Suitable alcohols are cyclohexanol, n-hexanol and phenol is a suitable phenol. Alcohol or phenol and mono- or dialkylamine recovered may be recycled. In examples:1-phenyl-3:3-dimethylurea is prepared by heating a mixture of aniline, cyclohexanol and urea until ammonia evolution ceases and then passing in dimethylamine whilst distilling off cyclohexanol (1); in similar processes 1-(p-chloro-phenyl)-3 : 3-dimethylurea is obtained using p-chloroaniline and dimethylamine as starting materials (2); 1-phenyl-3:3-dimethyl urea is obtained using aniline, phenol, urea and dimethylamine (3); in a similar process aniline, n-hexanol, urea and dimethylamine are used (4); and 1 - (31:41 - dichlorophenyl) - 3:3 - dimethylurea is obtained by a similar process to (1) using 3:4-dichloroaniline, urea, cyclohexanol and dimethylamine (5). The products in (1) and (2) may be purified by conversion to the hydrochlorides followed by hydrolysis. The products may be used in herbicidal compositions.ALSO:Herbicidal compositions comprise as an essential ingredient 1 - phenyl - 3 - 3 - dimethylurea, 1 - (p - choro - phenyl) - 3 - 3 - dimethylurea or 1 - (31 - 41 - dichlorophenyl) - 3 - 3 - dimethyl uear (see Group IV(b))
GB1550554A 1954-05-26 1954-05-26 Manufacture of substituted ureas Expired GB776069A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB1550554A GB776069A (en) 1954-05-26 1954-05-26 Manufacture of substituted ureas

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB1550554A GB776069A (en) 1954-05-26 1954-05-26 Manufacture of substituted ureas

Publications (1)

Publication Number Publication Date
GB776069A true GB776069A (en) 1957-06-05

Family

ID=10060313

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1550554A Expired GB776069A (en) 1954-05-26 1954-05-26 Manufacture of substituted ureas

Country Status (1)

Country Link
GB (1) GB776069A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102030684A (en) * 2009-09-25 2011-04-27 李其奎 Clean production method for symmetrical N,N'-dialkylurea

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102030684A (en) * 2009-09-25 2011-04-27 李其奎 Clean production method for symmetrical N,N'-dialkylurea

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