Sulfamic Acid → 3-methyl-4-(2,5-dichloro-4-fluorosulphonylphenylazo)-N-ethyl-N-(2-(3-cyanopropoxycarbonyl)ethyl)aniline

HRID 610438Notes

Reaction equation

HRID 610438 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([S:9]([F:12])(=[O:11])=[O:10])[C:6]([Cl:13])=[CH:5][C:3]=1[NH2:4].CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)CC.N(OS(=O)(=O)O)=O.[CH2:50]([N:52]([CH2:60][CH2:61][C:62]([O:64][CH2:65][CH2:66][CH2:67][C:68]#[N:69])=[O:63])[C:53]1[CH:58]=[CH:57][CH:56]=[C:55]([CH3:59])[CH:54]=1)[CH3:51].S(=O)(=O)(O)[NH2:71]>O.CO>[CH3:59][C:55]1[CH:54]=[C:53]([CH:58]=[CH:57][C:56]=1[N:71]=[N:4][C:3]1[CH:5]=[C:6]([Cl:13])[C:7]([S:9]([F:12])(=[O:11])=[O:10])=[CH:8][C:2]=1[Cl:1])[N:52]([CH2:50][CH3:51])[CH2:60][CH2:61][C:62]([O:64][CH2:65][CH2:66][CH2:67][C:68]#[N:69])=[O:63]

Participants

8

Reactant 5

HCID 5987Sulfamic AcidHCID 82157Nitrosylsulfuric acidHCID 153333614-Amino-2,5-dichlorobenzene-1-sulfonyl fluorideHCID 15333362N-ethyl-N-(2-(3-cyanopropoxycarbonyl)ethyl)-3-toluidineHCID 131720610Acetic propionic acid

Product 1

HCID 153333633-methyl-4-(2,5-dichloro-4-fluorosulphonylphenylazo)-N-ethyl-N-(2-(3-cyanopropoxycarbonyl)ethyl)aniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 2,5-dichloro-4-fluorosulphonylaniline (2 parts) and an acetic/propionic acid mixture (15 parts, 86/14 vol/vol), stirring at 0-5° C., was added dropwise nitrosylsulphuric acid solution (5 parts). The mixture was stirred at this temperature for a further 15 minutes. The diazo solution was added slowly to a mixture of N-ethyl-N-(2-(3-cyanopropoxycarbonyl)ethyl)-3-toluidine (2.6 parts), methanol (50 parts), water (20 parts) and sulphamic acid (0.5 part), stirring at 0-5° C. After stirring for 3 hours at this temperature, the product was isolated by filtration, washed with water and dried at 50° C. to yield 3-methyl-4-(2,5-dichloro-4-fluorosulphonylphenylazo)-N-ethyl-N-(2-(3-cyanopropoxycarbonyl)ethyl)aniline (2.6 parts). When applied to polyester materials from an aqueous dispersion, the dye (λmax=515 nm) gives bluish-red shades with excellent light fastness and excellent fastness to wet treatments.

Workup

  1. stirringstirring at 0-5° C
  2. stirringAfter stirring for 3 hours at this temperature
  3. customthe product was isolated by filtration
  4. washwashed with water
  5. customdried at 50° C.

Sources & evidence

ORD record
ord-3a070ca49f104d4eab7f160d17f944ab
Source dataset
uspto-grants-1999_12
Patent number
US05998592

Reaction notes

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