Chlorosulfonic acid → HCID 21392420, compound

HRID 461762Notes

Reaction equation

HRID 461762 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:12])=[C:9]([Cl:11])[Cl:10])[CH:5]=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14].Cl[S:18]([OH:21])(=O)=[O:19].[NH2:22]C1C=C(C(C)=C(Cl)Cl)C(S(Cl)(=O)=O)=CC=1S(Cl)(=O)=O>>[NH2:1][C:2]1[CH:7]=[C:6]([C:8]([CH3:12])=[C:9]([Cl:10])[Cl:11])[C:5]([S:18]([NH2:22])(=[O:21])=[O:19])=[CH:4][C:3]=1[S:13]([NH2:16])(=[O:15])=[O:14]

Participants

4

Reactant 3

HCID 24638Chlorosulfonic acidHCID 21392423HCID 21392423, compoundHCID 21392427HCID 21392427, compound

Product 1

HCID 21392420HCID 21392420, compound

Procedure

100 Mg. of the 2-amino-4-(1,1-dichloroprop-1-en-2-yl)benzenesulfonamide and 1.0 ml. of chlorosulfonic acid is mixed at 5° to 10° C. and then immersed into an oil bath of 100° to 110° for 1 hour. The reaction mixture is cooled in ice, added onto ice, extracted into CH2Cl2, the solution is washed twice with water, dried and concentrated in vacuo to yield 75 mg. of crude 4-amino-6-(1,1-dichloroprop-1-en-2-yl)-1,3-benzenedisulfonylchloride, identified by nuclear magnetic resonance and mass spectral analyses. 100 Mg. of this disulfonylchloride is then dissolved in 4 ml. of tertbutanol and ammonia gas is bubbled into the solution for about 10 minutes at room temperature. It is kept at room temperature for 15 minutes and then concentrated in vacuo. The residue is dissolved in ethyl acetate, washed with dilute aqueous HCl, water, dried and concentrated in vacuo to 87 mg. of crude product which slowly crystallized. It is recrystallized from a methanol-benzene-methylene-chloride mixture to give 4-amino-6-(1,1-dichloroprop-1-ene-2-yl)-1,3-benzenedisulfonamide with m.p. 199° to 202° C.

Workup

  1. temperatureThe reaction mixture is cooled in ice
  2. additionadded onto ice
  3. extractionextracted into CH2Cl2
  4. washthe solution is washed twice with water
  5. customdried
  6. concentrationconcentrated in vacuo
  7. customto yield 75 mg
  8. customof tertbutanol and ammonia gas is bubbled into the solution for about 10 minutes at room temperature
  9. waitIt is kept at room temperature for 15 minutes
  10. concentrationconcentrated in vacuo
  11. dissolutionThe residue is dissolved in ethyl acetate
  12. washwashed with dilute aqueous HCl, water
  13. customdried
  14. concentrationconcentrated in vacuo to 87 mg
  15. customof crude product which slowly crystallized
  16. customIt is recrystallized from a methanol-benzene-methylene-chloride mixture

Sources & evidence

ORD record
ord-a0f47f649e62481fa389f6d837adb4c6
Source dataset
uspto-grants-1977_12
Patent number
US04064239

Reaction notes

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