Sulfamic Acid → 4-(2-chloro-4-fluorosulphonyl phenylazo)-N-ethyl-N-benzyl aniline

HRID 1599202Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([F:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[NH2:8].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].C([O-])(=O)C.[Na+]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)CC.CO>[Cl:1][C:2]1[CH:3]=[C:4]([S:9]([F:12])(=[O:11])=[O:10])[CH:5]=[CH:6][C:7]=1[N:8]=[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

Participants

Conditions

Temperature: -5 °C

Procedure

3-Chloro-4-amino benzene sulphonylfluoride (1 part) was stirred in acetic/propionic acid 86/14 vol/vol (15 parts) and cooled to -5° C. Nitrosyl sulphuric acid solution (1.9 parts) was added dropwise then stirred at 0°-5° C. for 2 hours. The diazo solution was then added to a stirred mixture of N-ethyl-N-benzyl aniline (2.0 parts), methanol (50 parts), sulphamic acid (0.5 parts) and sodium acetate (5 parts) with ice/water (100 parts) at 0°-5° C. After stirring under these conditions for 1 hour, the dye was filtered off and washed well with water. The damp solid was slurried in methanol (100 parts) and re-filtered. Dried at 50° C. to yield the product 4-(2-chloro-4-fluorosulphonyl phenylazo)-N-ethyl-N-benzyl aniline (1.5 parts). When applied to polyester materials from an aqueous dispersion the dye gave orange shades. λmax 483 nm

Workup

stirringAfter stirring under these conditions for 1 hour
filtrationthe dye was filtered off
washwashed well with water
filtrationre-filtered
customDried at 50° C.

Sources & evidence

ORD record: ord-93752aba1eef4916b6bb765541a6b885
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739299

Reaction notes

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