Sulfamic Acid → 4-(4-chloro-5-fluorosulphonylphenylazo)-N,N-bis(2-cyanoethyl)aniline

HRID 1599207Notes

Reaction equation

HRID 1599207 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[S:9]([F:12])(=[O:11])=[O:10].N(OS(=O)(=O)O)=O.[C:20]([CH2:22][CH2:23][N:24]([CH2:31][CH2:32][C:33]#[N:34])[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)#[N:21].S(=O)(=O)(O)[NH2:36]>CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)CC.CO>[Cl:1][C:2]1[C:3]([S:9]([F:12])(=[O:10])=[O:11])=[CH:4][C:5]([N:8]=[N:36][C:28]2[CH:29]=[CH:30][C:25]([N:24]([CH2:23][CH2:22][C:20]#[N:21])[CH2:31][CH2:32][C:33]#[N:34])=[CH:26][CH:27]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 5987Sulfamic AcidHCID 73780Propanenitrile, 3,3'-(phenylimino)bis-HCID 82157Nitrosylsulfuric acidHCID 542778915-Amino-2-chlorobenzene-1-sulfonyl fluoride

Product 1

HCID 189309014-(4-chloro-5-fluorosulphonylphenylazo)-N,N-bis(2-cyanoethyl)aniline

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 131720610Acetic propionic acidSolvent

Procedure

2-Chloro-5-amino benzene sulphonylfluoride (2.1 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 and stirred at 0°-5° C. for 3 hours. The diazo solution was then added to a mixture of N,N-bis(2-cyanoethyl)aniline (2.1 parts), methanol (75 parts) and sulphamic acid (1 part) stirring in ice/water (75 parts) at 0°-5° C. Stirred under these conditions for 1 hour then allowed to stand at room temperature overnight before filtering off the dye. The solid was dried overnight to yield the product 4-(4-chloro-5-fluorosulphonylphenylazo)-N,N-bis(2-cyanoethyl)aniline (3.6 parts). The dye, when applied to polyester material from an aqueous dispersion, gave yellow shades. λmax 414 nm.

Workup

  1. temperaturecooled to 0°-5° C
  2. stirringStirred under these conditions for 1 hour
  3. waitto stand at room temperature overnight
  4. filtrationbefore filtering off the dye
  5. customThe solid was dried overnight

Sources & evidence

ORD record
ord-e399dca0492f441fbcb0c3713430c3d7
Source dataset
uspto-grants-1998_04
Patent number
US05739299

Reaction notes

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