Sulfamic Acid → 4-(2-chloro-5-fluorosulphonylphenylazo)-N-ethyl-N-benzyl aniline

HRID 1599201

Reaktionsgleichung

Reaktionsgleichung von HRID 1599201
[NH2:1][C:2]1[CH:3]=[C:4]([S:9]([F:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[Cl:8].N(OS(=O)(=O)O)=O.[CH2:20]([N:22]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:21].S(=O)(=O)(O)[NH2:37]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)CC.CO>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([S:9]([F:12])(=[O:11])=[O:10])=[CH:3][C:2]=1[N:1]=[N:37][C:26]1[CH:27]=[CH:28][C:23]([N:22]([CH2:20][CH3:21])[CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:24][CH:25]=1

Komponenten

7

Edukt 4

HCID 5987Sulfamic AcidHCID 7098N-Ethyl-N-benzylanilineHCID 82157Nitrosylsulfuric acidHCID 973833-Amino-4-chlorobenzenesulphonyl fluoride

Produkt 1

HCID 539697314-(2-chloro-5-fluorosulphonylphenylazo)-N-ethyl-N-benzyl aniline

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 131720610Acetic propionic acidLösungsmittel

Versuchsvorschrift

3-Amino-4-chloro benzene sulphonyl fluoride (2 parts) was stirred in acetic/propionic acid 86/14 vol/vol (25 parts) and cooled to 0°-5° C. Nitrosyl sulphuric acid solution (3.8 parts) was added dropwise at 0°-5° C. and stirred under these conditions for 2 hours. The diazo solution was then added to a mixture of N-ethyl-N-benzyl aniline (2.7 parts), methanol (100 parts) and sulphamic acid (1 part) stirring at 0°-5° C. After stirring under these conditions for 30 mins, ice/water (100 parts) was added and the mixture stirred for a further 1 hour. The product was isolated by filtration, washed with water and pulled dry. The damp solid was then slurried in methanol (100 parts) and refiltered. Dried at 50° C. to yield 4-(2-chloro-5-fluorosulphonylphenylazo)-N-ethyl-N-benzyl aniline (2.3 parts).

Aufarbeitung

  1. temperaturecooled to 0°-5° C
  2. stirringstirring at 0°-5° C
  3. stirringAfter stirring under these conditions for 30 mins
  4. stirringthe mixture stirred for a further 1 hour
  5. customThe product was isolated by filtration
  6. washwashed with water
  7. custompulled dry
  8. customDried at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-559d64b2333f46a0803664a50d614084
Quelldatensatz
uspto-grants-1998_04
Patentnummer
US05739299

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